Salesloft MCP Demo Server

# Customer Discovery Talking Points *5 Key Talking Points Per Persona for Salesloft + Clari Conversations* --- ## Enterprise Technology ### 1. Marcus Chen — CRO, Enterprise SaaS ($500M ARR) 1. **"Walk me through your current forecasting process—how do you roll up from rep to region to company?"** - Probe: How many systems touch the forecast? Who owns the data? - Listen for: Manual overrides, Excel consolidation, trust issues with rep commits 2. **"When a deal slips from one quarter to the next, how quickly do you know—and how do you prevent it?"** - Probe: Early warning signals, deal review cadence, CRM hygiene - Listen for: Surprise slips, lack of engagement data, after-the-fact analysis 3. **"You mentioned 8 tools in your stack—which ones actually get used daily vs. shelfware?"** - Probe: Adoption rates, data silos, rep complaints about admin burden - Listen for: "We have X but nobody uses it," integration pain, reporting gaps 4. **"How do you measure rep productivity today, and what would moving the needle by 20% mean for the business?"** - Probe: Activity metrics, time studies, selling time vs. admin time - Listen for: Lack of visibility, anecdotal evidence, no baseline measurement 5. **"When a rep leaves, how much institutional knowledge walks out the door?"** - Probe: Documentation, CRM notes, relationship mapping, handoff process - Listen for: Lost deals, customer complaints, ramp time for replacements --- ### 2. Jennifer Walsh — VP Sales, Mid-Market Software ($80M ARR) 1. **"You're scaling from 30 to 100 reps—what's your biggest fear about that growth?"** - Probe: Hiring, onboarding, playbook consistency, culture - Listen for: "What got us here won't get us there," unscalable processes 2. **"How do you currently capture what your top performers do differently?"** - Probe: Call recording, shadowing, coaching notes, win analysis - Listen for: Tribal knowledge, no systematic approach, manager variation 3. **"What's your pipeline coverage ratio target, and how confident are you in hitting it?"** - Probe: Historical accuracy, stage definitions, velocity assumptions - Listen for: "It depends," inconsistent stage criteria, gut-feel forecasting 4. **"If I followed a rep for a day, how much time would I see them actually selling vs. doing admin?"** - Probe: CRM updates, meeting prep, internal meetings, approvals - Listen for: Specific percentages, frustration, workarounds 5. **"When your CFO asks for ROI on your sales tech stack, what do you show them?"** - Probe: Attribution, baseline metrics, before/after comparisons - Listen for: "I don't have good data," faith-based investments, vendor-provided stats --- ### 3. David Okonkwo — CRO, Cybersecurity Platform ($200M ARR) 1. **"Security deals often stall in procurement—how do you maintain momentum when you're not in control?"** - Probe: Security questionnaires, vendor risk, legal review process - Listen for: Lack of visibility, champion access during review, competitor activity 2. **"In a market where speed wins, how do you balance thorough discovery with quick response times?"** - Probe: SDR qualification, SE availability, proposal turnaround - Listen for: Bottlenecks, competitive losses on speed, resource constraints 3. **"When you lose a deal to 'no decision,' what does your post-mortem look like?"** - Probe: Win/loss analysis, stakeholder mapping, pain quantification - Listen for: Lack of economic buyer access, poorly qualified pipeline, urgency creation 4. **"How consistently are your reps multi-threading into accounts—and how do you know?"** - Probe: Contact coverage, relationship mapping, engagement breadth - Listen for: Hero-based selling, single-threaded deals, champion risk 5. **"Technical sales cycles are extending—what's driving that and how are you adapting?"** - Probe: POC scope creep, competitive bake-offs, budget cycles - Listen for: SE burnout, unqualified technical evaluations, free consulting --- ### 4. Sarah Kim — VP Sales, Developer Tools ($45M ARR) 1. **"You're transitioning from PLG to sales-led—what signals tell you a user is ready for enterprise?"** - Probe: Usage thresholds, team size, feature requests, support tickets - Listen for: Disconnected product and sales data, reactive vs. proactive outreach 2. **"How do your developers feel about being sold to, and how does that shape your approach?"** - Probe: Messaging, channel preferences, self-serve vs. human touch - Listen for: Resistance to sales, community-based selling, bottom-up champions 3. **"Where does product usage data live, and how accessible is it to your sales team?"** - Probe: Data warehouse, CRM sync, PQL definitions, real-time vs. batch - Listen for: Data silos, engineering dependencies, stale information 4. **"Your SDRs are cold calling—what would it mean if they only called warm signals?"** - Probe: Efficiency, conversion rates, rep experience, prospect experience - Listen for: Wasted effort, brand damage, low connect rates 5. **"When you spot expansion potential, what's the motion to convert that to revenue?"** - Probe: Account teams, CS handoff, renewal plays, upsell triggers - Listen for: Reactive expansion, missed opportunities, timing issues --- ### 5. Robert Martinez — CRO, Cloud Infrastructure ($1.2B ARR) 1. **"With 6 product lines, how do you create a unified view of pipeline and forecast?"** - Probe: Systems, definitions, ownership, consolidation frequency - Listen for: Manual stitching, conflicting methodologies, delayed visibility 2. **"Cross-sell is underperforming by 40%—what's broken in the motion?"** - Probe: Territory design, comp, product knowledge, handoffs - Listen for: Siloed teams, double-crediting complexity, customer fatigue 3. **"How do you know if regional leaders are sandbagging or being realistic?"** - Probe: Commit accuracy history, bias detection, inspection methodology - Listen for: Distrust, gaming, unreliable roll-ups 4. **"After an acquisition, how do you integrate the sales org and systems?"** - Probe: Timeline, playbook alignment, system consolidation, culture - Listen for: Ongoing pain, duplicate processes, rep confusion 5. **"How real-time is your board's view into pipeline, and what do they ask for?"** - Probe: Reporting cadence, data lag, board meeting prep time - Listen for: Fire drills, stale data, lack of confidence --- ### 6. Amanda Foster — VP Sales, HR Tech ($120M ARR) 1. **"HR buying is seasonal—how do you build pipeline for Q4 budget flush?"** - Probe: Lead time, nurture programs, deal acceleration tactics - Listen for: Lumpy quarters, rushed deals, discounting pressure 2. **"Buying committees are expanding—how do you identify and engage all 8+ stakeholders?"** - Probe: Org chart mapping, multi-threading, content personalization - Listen for: Surprise stakeholders, late-stage blockers, decision delays 3. **"How long does it take to personalize an RFP response, and is that time well spent?"** - Probe: Content libraries, automation, win rates on RFPs - Listen for: Manual process, low win rates, resource drain 4. **"When competitors bundle with payroll, how do you compete on value vs. convenience?"** - Probe: Differentiation messaging, proof points, negotiation tactics - Listen for: Pricing pressure, feature comparison fatigue, bundling losses 5. **"CAC is up 45%—where is the efficiency leaking and how do you plan to fix it?"** - Probe: Channel mix, conversion rates, ACV trends, sales cycle length - Listen for: Unclear attribution, declining productivity, budget constraints --- ### 7. Michael Thompson — CRO, FinTech ($350M ARR) 1. **"Compliance extends your deals—how do you build that time into forecasts and plans?"** - Probe: Stage definitions, compliance probability, parallel workstreams - Listen for: Unpredictable delays, lack of compliance visibility, late surprises 2. **"When legal gets involved, how do you maintain momentum and visibility into redlines?"** - Probe: Contract tracking, escalation paths, standard terms acceptance - Listen for: Black box legal, deal stalls, rep frustration 3. **"Can you predict which prospects will pass compliance before you invest heavily?"** - Probe: Qualification criteria, early risk assessment, historical patterns - Listen for: Sunk cost on failed compliance, no predictive indicators 4. **"With 32% rep turnover, what's the cost of ramping replacements?"** - Probe: Ramp time to full productivity, training programs, mentorship - Listen for: Lost relationships, extended ramp, productivity dips 5. **"When a rep leaves mid-deal, how much do you lose and how do you recover?"** - Probe: CRM hygiene, handoff process, relationship continuity - Listen for: Lost context, customer complaints, deals stalling --- ### 8. Lisa Nakamura — VP Sales, AI/ML Platform ($60M ARR) 1. **"When prospects don't understand the category, how do you educate without extending the cycle?"** - Probe: Content strategy, qualification for readiness, market timing - Listen for: Long education cycles, tire-kickers, founder-led selling 2. **"There's no established playbook for AI sales—how are you building one?"** - Probe: Experimentation, win pattern analysis, coaching iteration - Listen for: Trial and error, inconsistent approaches, lack of data 3. **"POCs consume 80% of SE time—how do you qualify which ones are worth it?"** - Probe: POC criteria, success metrics, paid vs. unpaid, commitment signals - Listen for: Free consulting, no commitment, POC-to-close issues 4. **"Forecasting in a new category is hard—what's your current accuracy and approach?"** - Probe: Historical data, proxy metrics, stage definitions - Listen for: Wide variance, lack of benchmarks, gut-feel forecasting 5. **"Budget comes from unexpected line items—how do you discover where the money is?"** - Probe: Discovery process, stakeholder mapping, budget signals - Listen for: Long searches, multiple conversations, late discoveries --- ### 9. James Richardson — CRO, Data Analytics ($280M ARR) 1. **"Cloud providers are bundling analytics—how do you compete with 'good enough and free'?"** - Probe: Differentiation, value quantification, displacement messaging - Listen for: Feature comparison fatigue, pricing pressure, platform lock-in 2. **"Open-source alternatives are putting pricing pressure on you—how do you respond?"** - Probe: Total cost of ownership messaging, support value, enterprise features - Listen for: Discounting, lost deals on price, perception issues 3. **"Are customer success signals reaching sales before it's too late for expansion?"** - Probe: Data sharing, alert systems, CS-sales collaboration - Listen for: Reactive expansion, missed signals, organizational silos 4. **"Expansion revenue is declining as a percentage—what's changing?"** - Probe: Product usage patterns, competitive pressure, pricing structure - Listen for: Saturation, churn, insufficient coverage 5. **"How do you prevent reps from discounting too aggressively to win deals?"** - Probe: Approval workflows, discount guidelines, value selling training - Listen for: Margin erosion, lack of controls, inconsistent enforcement --- ### 10. Patricia Gonzalez — VP Sales, Integration Platform ($95M ARR) 1. **"Bottom-up adoption isn't converting to enterprise—what's the gap?"** - Probe: Expansion motion, executive engagement, value escalation - Listen for: Stuck in department, no executive sponsor, feature ceiling 2. **"Champions leave before deals close—how do you protect against that risk?"** - Probe: Multi-threading, relationship mapping, deal velocity - Listen for: Single-threaded deals, long cycles, champion dependency 3. **"Multi-year deals create cash flow challenges—how does that affect your strategy?"** - Probe: Deal structure preferences, financing options, board pressure - Listen for: Tension between sales and finance, forecasting complexity 4. **"Technical validation takes 3+ months—what's driving that and can it be compressed?"** - Probe: Integration complexity, resource availability, customer readiness - Listen for: Scope creep, unqualified technical requirements, SE burnout 5. **"Competitive displacement is your primary motion—how do you identify and prioritize targets?"** - Probe: Intent signals, competitive intelligence, timing triggers - Listen for: Spray and pray, lack of prioritization, missed windows --- ## Healthcare & Life Sciences ### 11. Dr. William Park — CRO, HealthTech SaaS ($180M ARR) 1. **"HIPAA concerns create bottlenecks—how early do you engage legal and compliance?"** - Probe: Qualification criteria, compliance pre-work, standard agreements - Listen for: Late-stage surprises, repeated reviews, lost deals 2. **"With 18-month cycles, how do you maintain engagement and prevent competitors from displacing you?"** - Probe: Nurture programs, relationship depth, value reinforcement - Listen for: Ghosting, competitor encroachment, champion fatigue 3. **"Clinicians on buying committees don't control budget—how do you navigate that?"** - Probe: Stakeholder mapping, clinical champion strategy, budget holder access - Listen for: Wrong-level engagement, stalled decisions, political complexity 4. **"Pilots rarely convert to enterprise—what's breaking in that transition?"** - Probe: Success criteria, expansion playbook, timing, stakeholder alignment - Listen for: No clear success metrics, change management, budget gaps 5. **"Reimbursement changes shift buyer priorities overnight—how do you stay aligned?"** - Probe: Market intelligence, messaging agility, pipeline requalification - Listen for: Reactive positioning, stale messaging, surprised by changes --- ### 12. Christina Patel — VP Sales, MedTech ($90M ARR) 1. **"Capital equipment budgets are frozen—how are you adapting your pitch?"** - Probe: ROI messaging, operational vs. capital positioning, financing - Listen for: Stalled deals, budget source pivots, creative deal structures 2. **"Value Analysis Committees add 6 months—can that be predicted or accelerated?"** - Probe: VAC engagement timing, clinical evidence prep, internal champions - Listen for: Unpredictable delays, repeated reviews, lack of visibility 3. **"Clinical evidence requirements vary by health system—how do you manage that?"** - Probe: Evidence library, customization, clinical affairs involvement - Listen for: Reinventing the wheel, resource drain, competitive gaps 4. **"How do you manage channel conflict when distributors and direct sales overlap?"** - Probe: Territory rules, compensation, deal registration, strategic accounts - Listen for: Internal competition, customer confusion, margin issues 5. **"GPO contracts limit pricing—how do you sell value in a commoditized environment?"** - Probe: Differentiation beyond price, service bundling, outcomes focus - Listen for: Margin pressure, RFP-driven buying, limited negotiation room --- ### 13. Anthony Williams — CRO, Life Sciences Software ($250M ARR) 1. **"R&D budgets are being cut—how is that affecting your pipeline and positioning?"** - Probe: Budget source shifts, efficiency messaging, competitive pressure - Listen for: Delayed decisions, increased scrutiny, longer cycles 2. **"21 CFR Part 11 validation extends implementation—how do you factor that into sales cycles?"** - Probe: Validation expertise, timeline setting, customer expectations - Listen for: Underestimated timelines, stalled implementations, churn risk 3. **"Global deals require region-by-region approval—how do you manage that complexity?"** - Probe: Regional stakeholders, local requirements, deal structure - Listen for: Fragmented decisions, long timelines, coordination challenges 4. **"Scientific buyers are skeptical of sales—what approach resonates with them?"** - Probe: Technical credibility, peer references, non-salesy engagement - Listen for: Resistance to traditional sales, peer influence, content preferences 5. **"The market is consolidating—how do you compete against larger integrated platforms?"** - Probe: Best-of-breed messaging, integration story, switching costs - Listen for: Platform pressure, bundle competition, strategic uncertainty --- ### 14. Rebecca Stone — VP Sales, Telehealth Platform ($55M ARR) 1. **"With 200+ competitors, how do you differentiate and avoid feature comparison battles?"** - Probe: Unique value, ideal customer profile, messaging discipline - Listen for: Commoditization, price competition, unclear positioning 2. **"Reimbursement policy changes create uncertainty—how does that affect buying behavior?"** - Probe: Customer concerns, risk mitigation, contract flexibility - Listen for: Delayed decisions, contract hesitation, budget uncertainty 3. **"Health system IT is overwhelmed—how do you get prioritized for implementation?"** - Probe: IT engagement, resource requirements, self-service options - Listen for: Long implementation queues, deprioritization, scope reduction 4. **"EHR integration requirements vary wildly—how does that affect deal complexity?"** - Probe: Pre-built integrations, scoping, pricing for custom work - Listen for: Unpredictable implementation, cost overruns, support burden 5. **"Retention is harder than acquisition—what's driving churn and how do you address it?"** - Probe: Churn analysis, customer success investment, value realization - Listen for: Usage issues, competitive displacement, unclear value --- ### 15. Daniel Lee — CRO, Clinical Trials Tech ($140M ARR) 1. **"Lead times between interest and budget are long—how do you qualify real opportunities?"** - Probe: Trial timing, budget visibility, sponsor relationships - Listen for: Premature pipeline, wasted resources, timing mismatch 2. **"Champions change with each new drug program—how do you build institutional relationships?"** - Probe: Multi-level engagement, company-wide value, relationship continuity - Listen for: Transactional relationships, restarting each deal, champion dependency 3. **"Global regulatory requirements fragment your sales—how do you manage regional complexity?"** - Probe: Local teams, compliance expertise, deal structure - Listen for: Inconsistent execution, compliance delays, resource gaps 4. **"Each therapeutic area needs different proof points—how do you scale that?"** - Probe: Reference library, therapeutic expertise, specialization - Listen for: Limited references, generalist positioning, credibility gaps 5. **"Your pipeline is 18-24 months out—how do you forecast with that visibility horizon?"** - Probe: Stage definitions, probability models, leading indicators - Listen for: Inaccurate forecasts, uncertainty, board pressure --- ### 16. Maria Santos — VP Sales, Healthcare Analytics ($70M ARR) 1. **"ROI takes 2+ years to prove—how do you sell value that's so delayed?"** - Probe: Leading indicators, case studies, risk mitigation - Listen for: Skeptical buyers, proof of value requirements, contract structures 2. **"Buyers want guaranteed outcomes—how do you structure contracts around that?"** - Probe: Risk sharing, performance guarantees, success metrics - Listen for: Outcome-based pricing, risk allocation, margin impact 3. **"Data integration is the primary barrier—how do you de-risk that for customers?"** - Probe: Implementation approach, data assessment, scoping - Listen for: Underestimated complexity, failed implementations, scope creep 4. **"How do you compete with health systems' internal analytics teams?"** - Probe: Build vs. buy messaging, capability gaps, speed to value - Listen for: Internal competition, credibility with data teams, budget sources 5. **"Sales cycles span multiple budget years—how do you maintain momentum?"** - Probe: Relationship management, milestone visibility, re-engagement - Listen for: Deal stalls, budget reauthorization, champion fatigue --- ### 17. Kevin O'Brien — CRO, Dental/Specialty Practice Software ($45M ARR) 1. **"Low ACVs mean you need volume—how do you balance quality and quantity?"** - Probe: Lead sources, qualification criteria, rep capacity - Listen for: Lead quality issues, rep burnout, conversion challenges 2. **"100K+ prospects is fragmented—how do you prioritize and reach them?"** - Probe: Segmentation, channel strategy, market coverage - Listen for: Spray and pray, inefficient coverage, messaging fatigue 3. **"Demo-to-close conversion is declining—what's driving that trend?"** - Probe: Demo quality, competitive dynamics, buyer behavior - Listen for: Unqualified demos, competitor pressure, changing expectations 4. **"Channel partners are cannibalizing direct—how do you manage that conflict?"** - Probe: Partner economics, territory rules, strategic accounts - Listen for: Revenue leakage, partner management complexity, friction 5. **"Owner-operators make emotional decisions—how does that change your sales approach?"** - Probe: Relationship selling, decision criteria, personal impact messaging - Listen for: Non-traditional sales motions, trust-based selling, referral reliance --- ### 18. Nancy Chen — VP Sales, Mental Health Platform ($35M ARR) 1. **"HR buyers have limited mental health budget—where else does the money come from?"** - Probe: Budget discovery, stakeholder expansion, value justification - Listen for: Budget constraints, creative sourcing, executive sponsorship 2. **"Clinical outcomes proof points take years—what do you sell in the meantime?"** - Probe: Intermediate metrics, case studies, credibility building - Listen for: Proof gaps, buyer skepticism, competitive differentiation 3. **"Privacy concerns are heightened for mental health—how do you address that in sales?"** - Probe: Security positioning, compliance, employee trust - Listen for: Deal blockers, legal requirements, employee adoption concerns 4. **"How do you differentiate from lifestyle wellness apps that cost a fraction?"** - Probe: Clinical value, outcomes focus, buyer education - Listen for: Price comparison, category confusion, perception issues 5. **"Your enterprise motion is immature—what's the path to building it?"** - Probe: Current state, talent, process, playbook development - Listen for: Founder-led sales, process gaps, scaling challenges --- ## Financial Services ### 19. Thomas Anderson — CRO, Banking Technology ($320M ARR) 1. **"Procurement cycles extend 18-24 months—how do you forecast and plan around that?"** - Probe: Pipeline management, stage definitions, resource allocation - Listen for: Unpredictability, long-term planning challenges, cash flow management 2. **"Vendor risk assessments take 6 months—can you predict which deals will pass?"** - Probe: Early qualification, risk assessment criteria, compliance pre-work - Listen for: Sunk costs, failed assessments, no predictive indicators 3. **"Legacy system integration is always required—how do you scope and price that?"** - Probe: Discovery process, implementation methodology, pricing models - Listen for: Scope creep, underestimated complexity, margin issues 4. **"How do you stay relevant when regulatory changes constantly shift priorities?"** - Probe: Market intelligence, messaging agility, advisory positioning - Listen for: Reactive positioning, lost relevance, timing mismatches 5. **"The CIO relationship seems more important than the product—how do you build it?"** - Probe: Executive engagement, relationship strategy, value demonstration - Listen for: Relationship-dependent selling, long cultivation, competitor incumbency --- ### 20. Victoria Price — VP Sales, Wealth Management Tech ($85M ARR) 1. **"M&A consolidation is changing your buyer landscape—how are you adapting?"** - Probe: Account strategy, relationship continuity, new buyer access - Listen for: Lost relationships, displaced champions, market shrinkage 2. **"Custodian integration is table stakes—what differentiates you beyond that?"** - Probe: Value proposition, unique capabilities, client outcomes - Listen for: Commoditization, feature parity, price competition 3. **"Advisors resist new technology—how do you drive adoption after the sale?"** - Probe: Implementation support, training, change management, CS involvement - Listen for: Churn risk, low utilization, adoption challenges 4. **"Long implementations delay revenue recognition—how does that affect your model?"** - Probe: Revenue timing, cash flow, deal structure, implementation capacity - Listen for: Backlog issues, resource constraints, finance tension 5. **"Competitive feature parity makes differentiation hard—where do you win?"** - Probe: Unique positioning, customer experience, service, outcomes - Listen for: Struggling to differentiate, price-based wins, messaging confusion --- ### 21. Richard Hughes — CRO, Insurance Technology ($150M ARR) 1. **"Carrier IT modernization keeps getting deprioritized—how do you create urgency?"** - Probe: Compelling event strategy, executive alignment, ROI quantification - Listen for: Stalled initiatives, competing priorities, budget shifts 2. **"Your growth expectations don't match carrier sales cycles—how do you manage that tension?"** - Probe: Investor expectations, pipeline building, efficiency focus - Listen for: Growth pressure, realistic planning, market timing 3. **"Actuarial teams are skeptical of AI/ML—how do you build credibility?"** - Probe: Technical validation, proof points, risk communication - Listen for: Trust barriers, technical credibility gaps, slow adoption 4. **"State-by-state regulations fragment your market—how do you scale?"** - Probe: Regulatory expertise, compliance approach, prioritization - Listen for: Complexity, resource drain, market focus decisions 5. **"Large carriers prefer to build—how do you compete with internal development?"** - Probe: Build vs. buy messaging, speed advantage, TCO arguments - Listen for: Lost to internal, positioning challenges, partnership models --- ### 22. Elizabeth Morgan — VP Sales, RegTech ($65M ARR) 1. **"Regulatory deadlines create urgency but also chaos—how do you capitalize on that?"** - Probe: Timing, readiness, competitive positioning, capacity planning - Listen for: Feast or famine, resource constraints, missed windows 2. **"Buyers want solutions before regulations are finalized—how do you sell into uncertainty?"** - Probe: Flexibility, regulatory intelligence, risk sharing - Listen for: Hesitant buyers, scope uncertainty, delayed decisions 3. **"Cross-border compliance needs multiple products—how do you position a complete solution?"** - Probe: Product portfolio, integration, packaging, partnerships - Listen for: Fragmented buying, solution gaps, competitive bundling 4. **"Chief Compliance Officers have limited budget authority—who else needs to be involved?"** - Probe: Stakeholder mapping, executive sponsorship, budget sources - Listen for: Wrong-level engagement, delayed decisions, budget constraints 5. **"When regulations stabilize, renewals are at risk—how do you maintain value?"** - Probe: Ongoing value, feature roadmap, relationship depth - Listen for: Churn after compliance, limited stickiness, competitive displacement --- ### 23. Christopher Taylor — CRO, Capital Markets Tech ($200M ARR) 1. **"Sell-side firms are cutting tech spend—where is budget still available?"** - Probe: Budget sources, value justification, efficiency messaging - Listen for: Budget constraints, prioritization, competitive pressure 2. **"Buy-side consolidation is reducing your prospect pool—how do you grow the pie?"** - Probe: Market expansion, new use cases, international growth - Listen for: Market saturation, TAM concerns, strategic pivots 3. **"Cloud migration in regulated environments is sensitive—how do you address concerns?"** - Probe: Security positioning, compliance, deployment options - Listen for: Cloud hesitation, hybrid requirements, regulatory barriers 4. **"Latency and performance are non-negotiable—how do you prove capability?"** - Probe: Technical validation, POC requirements, benchmarking - Listen for: Technical bar, testing requirements, competitive comparison 5. **"Pilots require significant investment before revenue—how do you qualify which are worth it?"** - Probe: Pilot criteria, commitment signals, success metrics - Listen for: Free POCs, conversion challenges, resource drain --- ### 24. Stephanie Clark — VP Sales, Commercial Lending Tech ($50M ARR) 1. **"Small banks have tiny budgets—how do you make the economics work?"** - Probe: Pricing models, implementation efficiency, support scaling - Listen for: Unit economics challenges, segmentation, service models 2. **"Credit unions buy differently than banks—how do you adapt?"** - Probe: Buying patterns, decision makers, value propositions - Listen for: Segment differences, messaging, sales motion variations 3. **"Core system integration is required for every deal—how do you manage that complexity?"** - Probe: Pre-built integrations, partnerships, scoping - Listen for: Integration pain, partner dependencies, scope expansion 4. **"Digital-first banks are competing for your customers—how do you differentiate?"** - Probe: Modern vs. legacy positioning, value proposition, target market - Listen for: Competitive pressure, positioning challenges, market shifts 5. **"Economic uncertainty is freezing lending tech purchases—how do you sell through that?"** - Probe: ROI messaging, risk mitigation, urgency creation - Listen for: Stalled pipeline, extended cycles, budget cuts --- ### 25. Andrew Miller — CRO, Accounting/Tax Technology ($175M ARR) 1. **"Buying only happens post-tax season—how do you build pipeline for that window?"** - Probe: Marketing timing, relationship nurturing, demo scheduling - Listen for: Seasonal challenges, pipeline management, revenue lumpiness 2. **"Generational transition in accounting firms—how do you engage next-gen leaders?"** - Probe: Buyer personas, channel preferences, messaging adaptation - Listen for: Changing buyers, new decision makers, technology expectations 3. **"Big 4 influence mid-market buying—how do you navigate that relationship?"** - Probe: Enterprise relationships, mid-market positioning, channel strategy - Listen for: Top-down influence, reference relationships, partnership opportunities 4. **"Embedded accounting in ERP is reducing your TAM—how do you compete?"** - Probe: Differentiation, specialization, best-of-breed positioning - Listen for: Platform competition, bundling pressure, value messaging 5. **"Desktop-to-cloud migration is slower than you expected—what's holding it back?"** - Probe: Migration barriers, customer concerns, change management - Listen for: Risk aversion, training needs, data migration concerns --- ## Manufacturing & Industrial ### 26. Frank Wilson — CRO, Industrial IoT ($130M ARR) 1. **"The OT/IT divide creates buying committee conflicts—how do you bridge that gap?"** - Probe: Stakeholder alignment, messaging per persona, champion strategy - Listen for: Organizational politics, siloed decisions, delayed projects 2. **"Factory floor pilots don't scale to enterprise—what's breaking in that transition?"** - Probe: Success criteria, expansion playbook, enterprise stakeholders - Listen for: Pilot purgatory, scale challenges, lack of executive sponsorship 3. **"ROI must be proven in hard dollars—how do you quantify operational improvements?"** - Probe: Metrics, baseline measurement, case studies, ROI methodology - Listen for: Soft benefits not valued, measurement challenges, skeptical buyers 4. **"Long procurement with many approvals—how do you accelerate without shortcuts?"** - Probe: Stakeholder mapping, parallel workstreams, champion coaching - Listen for: Bottlenecks, approval delays, lack of visibility 5. **"Your reps need deep technical knowledge—how do you hire and develop that?"** - Probe: Hiring profile, training programs, SE leverage, specialization - Listen for: Talent scarcity, ramp time, technical credibility gaps --- ### 27. Helen Cooper — VP Sales, Supply Chain Software ($95M ARR) 1. **"Post-pandemic urgency is fading—how do you maintain buyer priority?"** - Probe: Value messaging evolution, new pain points, urgency creation - Listen for: Delayed decisions, reprioritization, complacency 2. **"ERP vendors are expanding into supply chain—how do you compete?"** - Probe: Best-of-breed positioning, differentiation, integration story - Listen for: Platform competition, bundling losses, value erosion 3. **"Multi-year implementations delay value—how do you accelerate time to impact?"** - Probe: Implementation methodology, quick wins, phased approaches - Listen for: Long implementations, delayed value, churn risk 4. **"Global supply chain requires regional selling—how do you coordinate?"** - Probe: Regional teams, handoffs, global account management - Listen for: Coordination challenges, inconsistent execution, territory conflicts 5. **"Buyers have point solution fatigue—how do you position as strategic vs. tactical?"** - Probe: Platform positioning, strategic value, executive engagement - Listen for: Bundling pressure, crowded market, positioning challenges --- ### 28. George Baker — CRO, Manufacturing Execution Systems ($180M ARR) 1. **"CapEx budgets compete with capital projects—how do you win budget priority?"** - Probe: OpEx positioning, ROI, executive sponsorship, budget timing - Listen for: Budget competition, delayed projects, CapEx constraints 2. **"Implementation resources are the bottleneck—how do you scale capacity?"** - Probe: Partner ecosystem, implementation methodology, customer self-service - Listen for: Backlog, revenue recognition delays, resource constraints 3. **"Large SI relationships are required—how do you manage those partnerships?"** - Probe: Partner economics, deal registration, influence, joint selling - Listen for: Partner dependencies, margin sharing, relationship complexity 4. **"Vertical specialization is needed—how deep do you go by industry?"** - Probe: Industry expertise, use cases, references, messaging - Listen for: Generalist challenges, credibility gaps, competitive positioning 5. **"Legacy on-premise customers resist cloud—how do you drive migration?"** - Probe: Migration value, risk mitigation, hybrid options, timing - Listen for: Slow migration, security concerns, change management --- ### 29. Laura Martinez — VP Sales, Quality Management ($60M ARR) 1. **"Quality managers don't control budget—who's the real economic buyer?"** - Probe: Stakeholder mapping, executive engagement, value escalation - Listen for: Wrong-level engagement, delayed decisions, sponsor gaps 2. **"Compliance is seen as a cost center—how do you reframe as strategic?"** - Probe: Business value, risk quantification, executive messaging - Listen for: Perception challenges, budget limitations, priority issues 3. **"Paper-based processes are deeply entrenched—what triggers change?"** - Probe: Catalyst events, pain quantification, change management - Listen for: Status quo preference, inertia, resistance to change 4. **"FDA audit cycles drive purchasing windows—how do you time your approach?"** - Probe: Audit intelligence, timing, urgency, preparation selling - Listen for: Cyclical buying, narrow windows, missed timing 5. **"How do you compete with quality modules built into ERP?"** - Probe: Differentiation, compliance depth, specialization - Listen for: Feature comparison, bundling, good enough alternatives --- ### 30. Charles Davis — CRO, Industrial Marketplace ($110M ARR) 1. **"Supplier onboarding is your go-to-market bottleneck—how do you scale that?"** - Probe: Onboarding process, automation, incentives, resources - Listen for: Chicken-and-egg, supply gaps, onboarding friction 2. **"The chicken-and-egg problem between supply and demand—how do you solve it?"** - Probe: Market development strategy, seeding, anchor customers - Listen for: Marketplace dynamics, critical mass, growth strategy 3. **"Traditional distribution relationships resist your model—how do you navigate?"** - Probe: Channel strategy, value proposition to distributors, coopetition - Listen for: Channel conflict, resistance, relationship management 4. **"Long-tail SKUs have thin margins—where do you make money?"** - Probe: Unit economics, pricing strategy, volume plays - Listen for: Margin challenges, sustainability, business model validation 5. **"Enterprise buyers want procurement integration—how do you deliver that?"** - Probe: Integration capabilities, enterprise features, implementation - Listen for: Enterprise requirements, integration complexity, deal expansion --- ### 31. Diana Robinson — VP Sales, Maintenance Software ($45M ARR) 1. **"Maintenance managers buy tactically—how do you get strategic sponsorship?"** - Probe: Executive engagement, business value, upward selling - Listen for: Tactical decisions, limited budget authority, scope constraints 2. **"Demonstrating ROI requires production data—how do you access it for the sale?"** - Probe: Data discovery, baseline assessment, proof of concept - Listen for: Data access barriers, measurement challenges, estimation 3. **"Mobile workforce adoption varies—what drives successful rollouts?"** - Probe: Change management, training, user experience, quick wins - Listen for: Adoption barriers, training needs, technology resistance 4. **"Enterprise deals need C-suite sponsorship—how do you get there from maintenance?"** - Probe: Value escalation, executive messaging, champion coaching - Listen for: Limited access, strategic positioning challenges 5. **"How do you win against legacy point solutions that are 'good enough'?"** - Probe: Differentiation, total value, switching triggers - Listen for: Inertia, replacement resistance, switching cost concerns --- ## Retail & Consumer ### 32. Steven Wright — CRO, Retail Technology ($220M ARR) 1. **"Retail bankruptcies are shrinking your customer base—how do you grow anyway?"** - Probe: Market expansion, new segments, international, adjacencies - Listen for: TAM concerns, churn, market strategy 2. **"Unified commerce is table stakes—what differentiates you now?"** - Probe: Unique value, next-generation capabilities, customer outcomes - Listen for: Commoditization, feature parity, messaging challenges 3. **"Implementation during store hours is challenging—how do you minimize disruption?"** - Probe: Implementation methodology, phased rollouts, training - Listen for: Operational concerns, deployment complexity, change management 4. **"Multi-location rollouts take years—how do you accelerate and maintain momentum?"** - Probe: Rollout methodology, success metrics, stakeholder management - Listen for: Long implementations, executive fatigue, scope changes 5. **"IT buyer vs. Store Ops buyer conflict—how do you align both stakeholders?"** - Probe: Dual engagement, messaging per persona, alignment strategy - Listen for: Organizational friction, delayed decisions, competing priorities --- ### 33. Jennifer Adams — VP Sales, E-commerce Platform ($75M ARR) 1. **"Shopify dominates SMB—how do you compete at the bottom of the market?"** - Probe: Segmentation, differentiation, target market clarity - Listen for: Market positioning, competitive pressure, pricing 2. **"Enterprise deals require SI partnerships—how do you build and leverage those?"** - Probe: Partner ecosystem, deal dynamics, relationship management - Listen for: Partner dependencies, margin impact, coordination 3. **"Headless commerce is commoditizing the frontend—where's your value now?"** - Probe: Platform value, backend strength, flexibility positioning - Listen for: Commoditization, value erosion, differentiation 4. **"Marketing buyer vs. IT buyer—which do you target and why?"** - Probe: Buying center, primary persona, dual engagement - Listen for: Unclear buyer, varied approaches, alignment challenges 5. **"Platform migrations are high-risk for customers—how do you de-risk?"** - Probe: Migration methodology, phased approaches, success guarantees - Listen for: Migration fear, scope concerns, timeline anxiety --- ### 34. Paul Jackson — CRO, Consumer Brands Tech ($160M ARR) 1. **"CPG companies are consolidating vendors—how do you stay on the short list?"** - Probe: Strategic relationships, platform positioning, value breadth - Listen for: Vendor consolidation, competitive displacement, relationship depth 2. **"Retail media spend competes for your budget—how do you justify the investment?"** - Probe: Budget source, value comparison, ROI quantification - Listen for: Budget competition, new competitors, justification challenges 3. **"Enterprise CPG has long cycles—how do you forecast and plan around that?"** - Probe: Pipeline management, stage definitions, resource allocation - Listen for: Long cycles, forecasting challenges, cash flow management 4. **"Change management is the primary implementation barrier—how do you address it?"** - Probe: Change management methodology, training, executive sponsorship - Listen for: Adoption concerns, resistance, implementation complexity 5. **"How do you prove ROI against entrenched spreadsheet-based processes?"** - Probe: Value quantification, baseline measurement, quick wins - Listen for: Status quo competition, change resistance, ROI skepticism --- ### 35. Michelle Lee — VP Sales, Restaurant Technology ($40M ARR) 1. **"Franchisee vs. corporate buying—how do you navigate both decision makers?"** - Probe: Dual selling motion, corporate mandates, franchisee influence - Listen for: Decision complexity, fragmented buying, approval processes 2. **"Thin margins mean price sensitivity—how do you sell value in that environment?"** - Probe: ROI focus, cost reduction, efficiency gains - Listen for: Price pressure, value justification, margin sensitivity 3. **"Labor market challenges affect technology priorities—how do you align to that?"** - Probe: Labor efficiency messaging, automation value, hiring impact - Listen for: Shifting priorities, budget allocation, urgency 4. **"Integration with delivery platforms is required—how do you manage those dependencies?"** - Probe: Integration partnerships, delivery platform relationships - Listen for: Integration complexity, platform requirements, partner dynamics 5. **"High SMB churn—how do you balance acquisition cost with retention?"** - Probe: Churn analysis, CAC/LTV, retention strategies - Listen for: Unit economics, churn drivers, retention investments --- ### 36. Brian Garcia — CRO, Grocery/Food Tech ($85M ARR) 1. **"Grocery margins are razor thin—how do you justify technology investment?"** - Probe: ROI messaging, efficiency gains, shrink reduction - Listen for: Margin sensitivity, hard ROI requirements, skepticism 2. **"Kroger/Albertsons merger uncertainty—how are you planning around that?"** - Probe: Account strategy, scenario planning, diversification - Listen for: Concentration risk, strategic uncertainty, planning challenges 3. **"Technology decisions are made at banner level—how do you navigate that structure?"** - Probe: Organizational mapping, decision makers, approval processes - Listen for: Decentralized decisions, complex buying, relationship building 4. **"Fresh/cold chain complexity is unique—how do you demonstrate category expertise?"** - Probe: Vertical specialization, use cases, references - Listen for: Credibility needs, specialized requirements, expertise gaps 5. **"How do you compete with grocer's internal development teams?"** - Probe: Build vs. buy, speed advantage, TCO, partnership positioning - Listen for: Internal competition, relationship challenges, value proving --- ## Professional Services ### 37. Sandra Mitchell — CRO, Legal Technology ($140M ARR) 1. **"Law firm partners resist change—how do you drive adoption post-sale?"** - Probe: Change management, training, quick wins, executive sponsorship - Listen for: Adoption challenges, utilization issues, churn risk 2. **"Am Law 200 have complex procurement—how do you navigate that process?"** - Probe: Procurement relationships, legal dept buying, approval chains - Listen for: Long cycles, complex approvals, relationship requirements 3. **"Security and confidentiality are extreme—how do you meet that bar?"** - Probe: Security certifications, compliance, client confidentiality - Listen for: Security requirements, deal blockers, compliance burden 4. **"Corporate legal is a secondary buyer—how do you prioritize and engage?"** - Probe: Market segmentation, corporate legal motion, messaging - Listen for: Segment differences, opportunity sizing, sales motion variation 5. **"The billable hour model discourages efficiency—how do you sell productivity?"** - Probe: Value messaging, firm economics, alternative fee arrangements - Listen for: Misaligned incentives, value justification challenges --- ### 38. Mark Johnson — VP Sales, Consulting Tech ($55M ARR) 1. **"Consulting firms want to white-label—how do you structure those deals?"** - Probe: White-label economics, brand considerations, contract structures - Listen for: Margin impact, branding concerns, deal complexity 2. **"Project-based revenue recognition is complex—how does that affect forecasting?"** - Probe: Revenue timing, milestone billing, forecasting methodology - Listen for: Forecasting complexity, finance alignment, reporting challenges 3. **"Partner buy-in is required for adoption—how do you engage that level?"** - Probe: Executive engagement, partner relationship building, value messaging - Listen for: Top-down selling, access challenges, decision dynamics 4. **"Seasonal hiring cycles affect your pipeline—how do you plan around that?"** - Probe: Timing, pipeline management, marketing alignment - Listen for: Cyclical business, forecasting challenges, seasonality 5. **"Large firms prefer to build—how do you compete with internal development?"** - Probe: Build vs. buy, speed, expertise, partnership models - Listen for: Internal competition, lost deals, positioning challenges --- ### 39. Angela White — CRO, Staffing/Recruiting Tech ($95M ARR) 1. **"The staffing industry is cyclical—how do you build resilience for downturns?"** - Probe: Business model, customer diversification, product strategy - Listen for: Cyclical exposure, downturn planning, risk mitigation 2. **"Market is fragmented with many small agencies—how do you scale efficiently?"** - Probe: Segmentation, sales efficiency, channel strategy - Listen for: Unit economics, coverage challenges, market approach 3. **"VMS/MSP relationships control enterprise access—how do you navigate that?"** - Probe: Partnership strategy, integration, enterprise motion - Listen for: Gatekeepers, partnership requirements, access challenges 4. **"Direct hire vs. temp staffing need different products—how do you manage that?"** - Probe: Product portfolio, segmentation, sales specialization - Listen for: Product complexity, sales motion differences, focus 5. **"Indeed and LinkedIn are expanding—how do you compete with platform giants?"** - Probe: Differentiation, value proposition, partnership/competition - Listen for: Platform competition, existential concerns, positioning --- ### 40. Scott Harris — VP Sales, Architecture/Engineering Software ($65M ARR) 1. **"Autodesk dominates design—how do you coexist or compete?"** - Probe: Integration strategy, differentiation, partnership - Listen for: Platform dominance, integration requirements, positioning 2. **"Project-based software has long sales cycles—how do you maintain momentum?"** - Probe: Relationship management, project timing, pipeline management - Listen for: Long cycles, project dependency, timing challenges 3. **"Owner/operator firms vs. large ENR firms buy differently—how do you segment?"** - Probe: Segmentation, sales motion, pricing, messaging - Listen for: Segment differences, resource allocation, approach variation 4. **"CAD/modeling integration is required—how do you ensure compatibility?"** - Probe: Integration approach, technical validation, partnerships - Listen for: Integration complexity, technical requirements, testing 5. **"Infrastructure bill demand spike is fading—what's the new normal?"** - Probe: Market trends, pipeline sustainability, forecasting - Listen for: Demand normalization, planning adjustments, market outlook --- ## Media & Telecommunications ### 41. Timothy Brown — CRO, AdTech/MarTech ($170M ARR) 1. **"Privacy changes are disrupting targeting—how is your product adapting?"** - Probe: Product roadmap, privacy-first approach, customer communication - Listen for: Product concerns, competitive threats, strategic direction 2. **"Agency vs. brand direct sales differ—how do you resource and execute both?"** - Probe: Segment specialization, team structure, go-to-market - Listen for: Resource allocation, execution differences, prioritization 3. **"Walled gardens limit your platform value—how do you address that?"** - Probe: Platform strategy, integration, value proposition - Listen for: Competitive threats, strategic concerns, positioning 4. **"How do you prove incremental value over the existing tech stack?"** - Probe: ROI methodology, measurement, differentiation - Listen for: Value justification, measurement challenges, competition 5. **"Cookie deprecation timeline keeps shifting—how do you sell into that uncertainty?"** - Probe: Product flexibility, customer communication, risk mitigation - Listen for: Buyer hesitation, planning challenges, messaging --- ### 42. Rachel Green — VP Sales, Streaming/OTT Technology ($50M ARR) 1. **"Streaming wars are causing budget constraints—how do you prioritize opportunities?"** - Probe: Qualification, market segmentation, resource allocation - Listen for: Budget challenges, market dynamics, prioritization 2. **"Legacy broadcast vs. digital divide—which side do you focus on?"** - Probe: Market strategy, messaging, product positioning - Listen for: Market transition, strategic choices, resource focus 3. **"Technical buyers need detailed specs—how do you equip sales for that?"** - Probe: Sales engineering, technical content, buyer enablement - Listen for: Technical selling, resource needs, buyer expectations 4. **"Market consolidation reduces prospects—how do you grow the pie?"** - Probe: Market expansion, new use cases, adjacencies - Listen for: TAM concerns, growth strategy, market dynamics 5. **"Sports rights drive technology decisions—how do you time your approach?"** - Probe: Event timing, budget cycles, relationship building - Listen for: Cyclical opportunities, timing, relationship importance --- ### 43. Jeffrey Moore — CRO, Telecom Software ($125M ARR) 1. **"Carrier procurement is extremely slow—how do you forecast and staff for that?"** - Probe: Pipeline management, resource planning, forecasting - Listen for: Long cycles, planning challenges, resource allocation 2. **"5G investment is crowding out software budgets—how do you compete for spend?"** - Probe: Value positioning, budget justification, ROI - Listen for: Budget competition, prioritization, value messaging 3. **"Legacy system replacement is multi-year—how do you structure those deals?"** - Probe: Deal structure, milestones, revenue recognition - Listen for: Complex deals, contract negotiation, revenue timing 4. **"Network and IT organizations are misaligned—how do you bridge that?"** - Probe: Stakeholder management, dual engagement, alignment strategy - Listen for: Organizational friction, decision delays, complexity 5. **"MVNOs buy differently than carriers—how do you adapt your motion?"** - Probe: Segment differences, sales approach, product fit - Listen for: Segment variation, execution differences, prioritization --- ### 44. Catherine Hall — VP Sales, Gaming/Entertainment Tech ($70M ARR) 1. **"Creator economy is fragmented—how do you identify and reach high-value targets?"** - Probe: Segmentation, marketing, qualification - Listen for: Market fragmentation, targeting challenges, efficiency 2. **"Platform dependencies create risk—how do you mitigate that for customers?"** - Probe: Multi-platform, risk messaging, product strategy - Listen for: Platform risk, customer concerns, strategic positioning 3. **"Low ACVs require high-volume motion—how do you scale efficiently?"** - Probe: Sales efficiency, automation, self-service - Listen for: Unit economics, scaling challenges, motion design 4. **"Seasonal cycles around game releases—how do you plan for that?"** - Probe: Pipeline timing, marketing alignment, forecasting - Listen for: Seasonality, planning challenges, revenue lumpiness 5. **"Enterprise gaming studios have slow procurement—how do you parallel-path?"** - Probe: Enterprise motion, stakeholder management, deal acceleration - Listen for: Long cycles, resource allocation, opportunity qualification --- ## Education & Government ### 45. Ronald King — CRO, EdTech K-12 ($100M ARR) 1. **"ESSER funding cliff is creating a crisis—how are you helping customers plan?"** - Probe: Customer advisory, sustainability planning, value messaging - Listen for: Funding concerns, churn risk, strategic response 2. **"Procurement cycles are tied to school year—how do you manage seasonal pipeline?"** - Probe: Timing, pipeline management, marketing alignment - Listen for: Seasonality, planning, resource allocation 3. **"Superintendent turnover disrupts deals—how do you protect against that?"** - Probe: Multi-threading, relationship continuity, deal velocity - Listen for: Champion risk, deal stalls, relationship management 4. **"State-level adoption varies—how do you prioritize and approach different states?"** - Probe: Market prioritization, state strategies, resource allocation - Listen for: Geographic complexity, regulatory variation, focus 5. **"COPPA and FERPA complexity—how do you turn compliance into competitive advantage?"** - Probe: Compliance positioning, security messaging, differentiation - Listen for: Compliance burden, competitive positioning, deal enablement --- ### 46. Emily Turner — VP Sales, Higher Ed Technology ($60M ARR) 1. **"Enrollment declines affect budgets—how do you sell value in that environment?"** - Probe: ROI messaging, efficiency gains, student outcomes - Listen for: Budget constraints, value justification, skepticism 2. **"Faculty resist technology change—how do you drive adoption post-sale?"** - Probe: Change management, training, quick wins, stakeholder engagement - Listen for: Adoption challenges, utilization, churn risk 3. **"Buying cycles span academic years—how do you maintain momentum?"** - Probe: Relationship management, timing, pipeline management - Listen for: Long cycles, timing challenges, deal stalls 4. **"Grants create unpredictable timing—how do you forecast around that?"** - Probe: Grant intelligence, pipeline management, forecasting - Listen for: Timing uncertainty, budget variability, planning 5. **"SIS integration is required—how do you ensure compatibility?"** - Probe: Integration approach, partnerships, technical validation - Listen for: Integration complexity, partner dependencies, scope --- ### 47. Joseph Harris — CRO, GovTech ($150M ARR) 1. **"FedRAMP certification timeline and cost—where are you in the process?"** - Probe: Certification status, investment, competitive positioning - Listen for: Compliance readiness, competitive gaps, timeline 2. **"Contract vehicles limit go-to-market—which vehicles do you have?"** - Probe: Vehicle strategy, partnerships, market access - Listen for: Vehicle coverage, gaps, partnership needs 3. **"Fiscal year-end creates feast-or-famine—how do you smooth revenue?"** - Probe: Pipeline management, deal timing, capacity planning - Listen for: Seasonality, resource management, forecasting 4. **"State and local budgets are constrained—how do you justify investment?"** - Probe: ROI messaging, federal funding pass-through, value - Listen for: Budget constraints, value justification, competition 5. **"Long cycles with multiple approvals—how do you accelerate without shortcuts?"** - Probe: Stakeholder management, parallel processes, visibility - Listen for: Approval complexity, timing, resource allocation --- ### 48. Donna Martinez — VP Sales, Corporate Training ($45M ARR) 1. **"The CLO role is disappearing—who's the new buyer?"** - Probe: Buyer evolution, stakeholder mapping, messaging - Listen for: Buyer shifts, access challenges, positioning 2. **"Training budget is first cut in downturn—how do you defend renewals?"** - Probe: Value proof, executive sponsorship, ROI - Listen for: Churn risk, budget vulnerability, retention strategy 3. **"Proving skills development ROI is difficult—what metrics do you use?"** - Probe: Measurement methodology, leading indicators, case studies - Listen for: Proof challenges, buyer skepticism, value articulation 4. **"Content vs. platform buying decisions—which do you lead with?"** - Probe: Product positioning, buyer priorities, bundling - Listen for: Value perception, competitive dynamics, positioning 5. **"LMS commoditization at low end—how do you differentiate?"** - Probe: Differentiation, target market, value proposition - Listen for: Competitive pressure, positioning, market focus --- ## Emerging Markets/Specialty ### 49. Christopher Lane — CRO, Sustainability/ESG Tech ($80M ARR) 1. **"Regulatory requirements are still evolving—how do you sell into uncertainty?"** - Probe: Flexibility, regulatory intelligence, risk mitigation - Listen for: Buyer hesitation, scope uncertainty, timing 2. **"Buyers don't know which frameworks matter—how do you guide them?"** - Probe: Advisory positioning, framework expertise, education - Listen for: Confusion, framework proliferation, guidance needs 3. **"CFO vs. CSO vs. Legal—who's the real buyer?"** - Probe: Buying center, stakeholder dynamics, primary contact - Listen for: Unclear ownership, multi-stakeholder complexity, access 4. **"Data collection is the primary barrier—how do you de-risk implementation?"** - Probe: Implementation approach, data assessment, phased rollouts - Listen for: Implementation concerns, scope anxiety, risk 5. **"You're competing with spreadsheets and consultants—how do you displace?"** - Probe: Differentiation, switching triggers, value proposition - Listen for: Status quo competition, consultant relationships, change drivers --- ### 50. Jessica Adams — VP Sales, PropTech ($55M ARR) 1. **"CRE market downturn is affecting budgets—where is spending still happening?"** - Probe: Budget sources, resilient segments, value messaging - Listen for: Market dynamics, opportunity pockets, adaptation 2. **"Landlord vs. tenant vs. broker—which buyer do you prioritize?"** - Probe: Segmentation, primary buyer, go-to-market - Listen for: Buyer complexity, segment focus, resource allocation 3. **"Property-level data is fragmented—how do you solve that for customers?"** - Probe: Data integration, implementation approach, value delivery - Listen for: Data challenges, implementation complexity, value creation 4. **"Asset management decisions have long cycles—how do you stay relevant?"** - Probe: Relationship management, nurturing, timing - Listen for: Long cycles, relationship building, pipeline management 5. **"Market recovery timing is uncertain—how are you planning for different scenarios?"** - Probe: Scenario planning, strategic flexibility, customer communication - Listen for: Uncertainty, planning challenges, strategic direction --- ## Quick Reference: Discovery Question Framework | Question Type | Purpose | Example Opener | |--------------|---------|----------------| | **Process** | Understand current state | "Walk me through..." | | **Pain** | Quantify problem | "When X happens, what's the impact?" | | **Metrics** | Establish baseline | "How do you measure...?" | | **Decision** | Understand buying process | "Who else needs to be involved?" | | **Vision** | Understand desired state | "What would success look like?" | --- *Customer Discovery Talking Points for Salesloft + Clari Sales Conversations* *Reference: [Salesloft-Clari Merger](https://www.salesloft.com/clari-salesloft-merger)*