Salesloft MCP Demo Server

# Customer Interview Transcript: Paul Jackson, CRO ## Consumer Brands Tech | $160M ARR **Date:** January 8, 2025 **Duration:** 32 minutes **Participants:** - Paul Jackson, Chief Revenue Officer, Consumer Brands Tech - Sarah Chen, Enterprise Sales Director, Salesloft + Clari - David Torres, Solutions Engineer, Salesloft + Clari **Location:** Virtual (Zoom) **Background:** Discovery call following initial outreach about sales execution and revenue intelligence platform consolidation --- ## Interview Transcript **[00:00-01:15] Opening & Context Setting** **Sarah:** Paul, thanks so much for taking the time. We know you're incredibly busy, so I want to be really respectful of your time today. What I'd love to do is understand what's happening in your world right now—specifically around sales operations, how you're thinking about your tech stack, and maybe where some of the friction points are. **Paul:** Absolutely, I appreciate you jumping straight in. Look, we're at an interesting moment. We've gone from kind of a Wild West on the sales side to trying to get some actual rigor. We hit $160M ARR last year, but frankly, we did it somewhat by accident. We had great products and great sales teams, but the visibility? The predictability? That's been rough. **Sarah:** That's a super honest opening. When you say by accident, what do you mean? **Paul:** I mean we had amazing win rates and deal sizes, but if you asked me three months ago what our pipeline would close at, I'd probably be off by 15, 20, sometimes 30 percent. That's not acceptable at this scale. And it's hard to talk to investors, board members, or frankly plan the business when you don't know what's actually going to land. **David:** That lack of visibility—is that more about pipeline accuracy, deal-by-deal forecasting, or something broader? **Paul:** All of it, honestly. Pipeline quality, deal-by-deal visibility, rep activity patterns. We have eight sales regions across different verticals—traditional CPG, DTC, retail partners. The way a deal moves is different in each one, and we're trying to apply one uniform process when the reality is messier. --- **[01:15-06:30] Vendor Consolidation & Strategic Relationships** **Sarah:** Let's zoom out for a second. You've got—what—how many sales tech vendors are you currently working with? **Paul:** Way too many. *[laughs]* We've got Salesforce as our CRM, obviously. Then Outreach for cadences and multi-touch, a Gong-like platform for call recording and analytics, Tableau for reporting, a custom pipeline forecasting model in Looker that nobody really trusts, Slack integrations everywhere, and we've got people still using spreadsheets for deal reviews because—honestly—they're faster than the tools. **David:** Do you have visibility into whether deals are moving in Salesforce before they close? **Paul:** Not really. That's been a huge pain point. A deal might be stuck in Stage 3 for two months, and nobody knows if it's actually at risk, if the rep is just lazy about updating it, or if there's a real blocker. We had a deal we thought was coming in Q4 that fell through in November. The rep had updated it correctly in Salesforce, but nobody was paying attention. **Sarah:** So the data is there, but the visibility isn't. **Paul:** Exactly. That's why people revert to spreadsheets. Our VP of Sales sends out a custom spreadsheet template every week to each region, and regions fill it in manually with their own commentary. Then it all goes into a quarterly business review in PowerPoint. It works, but it's insane. It's seven days of data entry and manual consolidation. **Sarah:** And when you think about consolidating vendors, what does that actually mean for you? Is it about having fewer contracts to manage, or is it more about having one system that talks to all the others? **Paul:** Both, actually. Fewer contracts matters—our procurement team would love that. But what really matters is one place where my sales leaders can see the complete picture. Right now, Outreach tells me about activity, Salesforce tells me about deal movement, Gong tells me what they said on calls, but there's no connective tissue. It's like having four different news feeds about the same customer and trying to make a decision. **David:** When you say "complete picture," what would that look like operationally? **Paul:** A view where I can see: This rep is working this deal. Here's their activity last week. Here's where we are in the buying process based on what they've actually said on calls. Here's whether that's on track for this quarter or next. And here's what they need to do next to move it forward. And I need that for all 80 reps across my organization, updateable in real-time, not in a weekly spreadsheet. **Sarah:** That's incredibly specific. Has Salesforce tried to solve that? **Paul:** Their revenue intelligence features are okay, but Salesforce feels like it was built to manage deals, not to predict them. Every time they add a new feature, it feels like it's bolted on. We don't trust their forecasting. And adding more stuff to Salesforce means more training, more configuration, more maintenance. At this point, we're asking: do we want a best-of-breed partner who specializes in this, or do we want to layer more features onto Salesforce? **Sarah:** And that's driving you toward consolidation around a specialized platform rather than going deeper into Salesforce? **Paul:** Yeah. If I could have one integrated system that was built for sales execution and forecasting from the ground up, with Salesforce as the system of record, that would change the game. It would take our sales team's time out of data entry and put it into selling. --- **[06:30-11:45] Budget Pressures & Retail Media Competition** **Sarah:** Let's talk about budget for a second. In a consumer brand company, how are sales tech budgets typically allocated? **Paul:** *[sighs]* That's the million-dollar question. We have a total headcount budget, a marketing budget, and an operations budget. Sales tech lives under operations. But here's the problem: marketing is exploding right now. Retail media is a huge growth driver for us, and that budget is competing directly with every sales function budget we have. **David:** Walk me through that. Why does retail media compete with sales operations? **Paul:** Because we're funded by the same P&L owner at the executive level. The CFO sees: "We can spend a million dollars on a sales execution platform, or we can invest that million in retail media advertising and get direct ROI on CPG sell-through." Retail media is measurable, immediate, and touches the consumer directly. It's seductive to finance. **Sarah:** But those aren't either/or decisions, right? Shouldn't they fund different things? **Paul:** You'd think so. But our CEO is pushing for direct-to-consumer and direct-to-retail relationships. If we can control the shelf and the media narrative, we don't need to wait for customers to find us. So retail media gets massive prioritization. And that means sales operations budgets are getting scrutinized harder. **David:** So when we're talking about ROI, we're competing against what retail media can show—which is pretty concrete, right? Lower CAC, direct revenue impact. **Paul:** Exactly. Retail media spend is tied to a particular brand's profit and loss. If we spend $100K on retail media for Product X, we can measure the lift in sell-through. It's direct. With a sales execution platform, the ROI is more indirect: better forecasting, higher deal win rates, faster cycle times. Those are real, but they're harder to point to. **Sarah:** How do you think about quantifying ROI on a sales transformation? **Paul:** That's where I'm stuck, honestly. I know intuitively that if we could reduce cycle time by 10 percent, that's huge. Our average deal is $400K and our average cycle is 7 months. If we compress that to 6.5 months, we'd probably add $5-8M in incremental ARR from better pipelining alone. But proving that a platform caused that? That's where it gets fuzzy. **David:** What if we started with a baseline—measured your current state for two months, then implemented, then measured for two months after? **Paul:** I'd be into that. We don't have a baseline currently. We have this fuzzy sense that things could be better, but without data, we can't make the business case to the CFO. And frankly, that's embarrassing at $160M ARR—we should know our own metrics cold. **Sarah:** So part of the conversation with your CFO is going to be: "Here's where we are today, here's what we'll measure, here's what success looks like"? **Paul:** Yes. And I need to be honest about this: retail media will probably win in our budget round this year. But if I can show that a consolidated sales platform could drive 5-8 percent improvement in deal velocity, that becomes a conversation for 2026. **David:** That's fair. But that also means we should be thinking about a pilot or a phased approach—something that doesn't require a massive upfront investment but lets you test the model. **Paul:** I'm definitely open to that. What would that look like? --- **[11:45-18:20] Enterprise CPG Sales Cycles & Pipeline Management** **Sarah:** Let me ask about the sales motion itself. CPG is interesting because you've got some really long sales cycles. Walk me through what a typical deal looks like for you. **Paul:** So we have three main customer segments. One is traditional retail partners—grocery chains, convenience store chains. Those are long, complex, political deals. You're selling to the procurement team, the marketing team, sometimes the CEO. These deals are typically $1-3M and can take 8-14 months. **David:** That's long. What's driving the length? **Paul:** Multiple approval layers. We're asking them to integrate with our platform, change how their merchandising teams work, potentially change their media strategy. For a big retailer, that's an existential business decision. They need board approval, IT security review, legal review, vendor negotiations. It's not one decision; it's a series of gate reviews. **Sarah:** So the deal doesn't move linearly. **Paul:** Not at all. We might be in Stage 3—Validation—for four months. We're doing pilots, we're showcasing ROI, we're bringing in their team and our product team to align. Then we move to Stage 4—Negotiation—and that could be another three months of contract back-and-forth. **David:** How are you currently defining those stages? **Paul:** *[laughs]* That's the problem. It's not consistent. Some reps see it as: Initial Meeting, Qualified, Demo, Pilot, Negotiation, Closed. Others see it as: Prospect, Lead, Opportunity, Advanced, Closed. One region sees it as: One, Two, Three, Four, Five. We literally have reps interpreting the pipeline differently. **Sarah:** And that makes forecasting impossible. **Paul:** Absolutely. If I ask a rep, "Where is this deal?" They'll say "Stage 3" and I have no idea if that means they've had one meeting, they've done a full pilot, or they've been stuck waiting for a customer approval for two months. **David:** What would it take to standardize that? **Paul:** We've tried. Our VP of Sales has tried to push a standardized stage definition. But reps resist because their deals move differently. A DTC customer might go from Prospect to Closed in 6 weeks. A big retailer goes Prospect to Closed in 12+ months. Same rep, same product, totally different timeline. **Sarah:** So you need a system that can understand different deal types, not just different stages. **Paul:** Yes. We have deal types that are industry-specific. DTC tech, traditional retail, media networks, enterprise tech. Each one has a different timeline, a different buyer constellation, a different decision-making process. A system that could account for that would be revolutionary. **David:** How many reps are you managing across those customer types? **Paul:** Eighty direct salespeople, plus customer success team. But we also have a regional sales leadership team—eight VPs of Sales. Each one is responsible for their own region and customer type. They're the ones doing the weekly deals reviews with their teams. **Sarah:** So the forecasting bottleneck is at the regional VP level. **Paul:** Exactly. I meet with my VPs every other week. They come with updated spreadsheets, they tell me which deals are at risk, which are advancing, which are new. But if I want to spot-check a deal, I have to dig into Salesforce, which is a disaster. The data in Salesforce doesn't reflect what the VP just told me because the VP has newer information that they haven't entered yet. **David:** That's the gap between reality and the system of record. **Paul:** That's exactly the gap. And it's a real problem when you're trying to manage a $160M business. You're making decisions based on incomplete information. And the reps are frustrated because they're updating two systems—their CRM and the weekly spreadsheet. **Sarah:** How much time per week do you think goes into that spreadsheet? **Paul:** Each rep, maybe 30 minutes on Friday to do their update. Each regional VP, probably 4-5 hours to consolidate their region, clean up data, add commentary. And then at my level, I'm spending probably 6 hours a week on pipeline analysis and forecasting. **David:** So if you could cut that in half with better tooling, that's meaningful hours of selling time recovered. **Paul:** That's the pitch, right? But right now, those spreadsheets feel sticky because they're adaptable. If a deal has a weird dynamic, the rep can just type a note. A system has to be flexible enough to handle the complexity but structured enough to give me clarity. --- **[18:20-24:30] Change Management & Organizational Adoption** **Sarah:** Let's talk about the elephant in the room: Change management. We've seen so many platforms fail not because they're bad, but because organizations can't adopt them. Where do you think you'd run into friction? **Paul:** *[long pause]* Honestly, with my reps and my sales leaders. They're going to see this as more work, not less work. They're going to think: "I've got my way of doing things, it works, now I have to learn a new system." **David:** Has Salesforce adoption gone smoothly? **Paul:** We spent two years trying to get good adoption of Salesforce. We had dedicated implementation teams, we did training, we sent out documentation. And we still have reps who don't use it properly. They'll create the opportunity in Salesforce, but they'll do the actual deal management in email and spreadsheets because that's easier. **Sarah:** So what would need to be different with a new platform? **Paul:** Executive sponsorship, honestly. If our CEO and CFO and I are all behind it, saying "This is how we're going to run the business," that changes the game. But if it's positioned as "Hey, here's another tool," it fails. **David:** How would you create that sponsorship? **Paul:** I'd need to show the business impact first. Do a pilot with one region, demonstrate the value, show the time savings, show the forecast accuracy improvement. Then go to the executive team and say, "Here's what's possible if we do this across the entire business." **Sarah:** Walk me through what that pilot would look like. **Paul:** I'd probably start with our West Coast region. That's got about 12 reps, mostly focused on DTC and emerging tech companies. Shorter deal cycles, more consistent deal progression. Over 60-90 days, we'd migrate them to the new platform, run parallel tracking with the old system, measure the differences in forecast accuracy, cycle time, and activity levels. **David:** And what would success look like? **Paul:** Better forecast accuracy—getting to within 5 percent instead of 15-20 percent off. Faster cycle times. And honestly, rep happiness. If reps spend less time on data entry and more time selling, they'll be happier. **Sarah:** How much time would you need to invest in training and change management? **Paul:** That's where I'd probably need help. I could dedicate one person internally—maybe someone from my ops team. But we'd need a partner who could run the methodology training, work with the regional VPs to define processes, and support the rollout. **David:** Would that person be dedicated full-time? **Paul:** Maybe 60 percent? They'd also have to manage our ongoing Salesforce stuff. But yeah, this would need real organizational resources. **Sarah:** What would the timeline look like? **Paul:** Pilot in Q1, decision point in Q2. If the pilot works, full rollout across all eight regions in Q3 and Q4. We'd probably do it by region so we don't disrupt the whole organization at once. **David:** And that timeline assumes board and executive buy-in by Q2? **Paul:** Yeah, which brings us back to the ROI question. I need to show the pilot results and make the business case. That's the gating factor. --- **[24:30-30:45] Baseline Measurement & Quick Wins** **Sarah:** Let me ask about quick wins. You mentioned that retail media gets funded because of direct ROI. Are there any quick wins we could show in a sales transformation that would help build momentum? **Paul:** Yes, actually. If we could reduce our average cycle time by just one month, that would be huge. One month across an eighty-rep organization—that's material revenue impact. Let me do the math real quick: we've got about 30 open opportunities across our sales team at any given time. If each one is $400K and we compress the timeline by a month, that's $400K in incremental ARR from better pipelining alone. Times twelve months, that's probably $4-5M in net ARR impact. **David:** That's the kind of thing you could show the board. **Paul:** Exactly. But I have to measure it. What's our baseline cycle time today? I don't actually know. I can estimate it's 7-8 months average, but we haven't measured it properly. That's embarrassing. **Sarah:** So the first step would be establishing that baseline. What would that take? **Paul:** Analytics. We'd need to pull every closed deal from the last 12 months, calculate the time from first opportunity creation to close date, and understand the variance by deal type and region. We probably have that data in Salesforce, but I'd need my ops team to spend time pulling it. **David:** Would it be helpful if we could do that for you as part of the pilot proposal? **Paul:** That would actually be really valuable. If you could come back to me with "Here's your current state—average 7.2 months, variance of 2-14 months by customer type—and here's what's driving the variance," that would help me build the business case. **Sarah:** And then we'd measure the same way after the pilot and compare. **Paul:** Yes. And realistically, if we can move the needle by 10-15 percent in the pilot, that's a win. **David:** Are there other quick wins beyond cycle time? **Paul:** Forecast accuracy is huge. And visibility. If my sales leaders can open a dashboard and know exactly where their deals stand without a Friday spreadsheet update, that's a win. If a rep spends 30 minutes less per week on data entry, that's a win. **Sarah:** What's your timeline for making a decision on moving forward? **Paul:** I need to talk to my CFO, probably in late January. If we can position this as a pilot with clear success criteria and low risk, I think I can get budget approval for Q1. The full rollout depends on the pilot results. **David:** So realistically, we're looking at a pilot kick-off in February or March? **Paul:** If we can get the business case to the CFO by the end of January, yes. Pilot kick-off in mid-February, results in April, decision on rollout in May. **Sarah:** That works for us. What happens between now and our next conversation? **Paul:** I'd like you to send over a proposal that includes: 1. The baseline measurement analysis—our current state 2. Pilot scope for the West Coast region 3. Success criteria and how we'd measure them 4. Implementation timeline and resource requirements 5. Total cost of ownership for the pilot plus full rollout 6. Reference customers in CPG or retail space **Sarah:** We can get you that. And then what? **Paul:** I'll share it with my executive team, probably in the next two weeks. Depending on their questions and concerns, we'll either move to pilot discussions or we'll need another conversation. **David:** Perfect. And if there are questions, we can hop on a call to discuss. **Paul:** Yeah, that would be helpful. I know I'm probably the most skeptical person on my team about new platforms, so having someone who can answer detailed questions about how this would work for us would go a long way. --- **[30:45-32:15] Closing & Next Steps** **Sarah:** Paul, I appreciate your honesty throughout this conversation. You've been really clear about what's working and what's not. That's actually rare and really helpful. **Paul:** I appreciate you asking the right questions. A lot of vendors come in with their pitch, and they don't actually try to understand how we operate. You spent the time to understand our customer types, our timeline challenges, our organizational dynamics. That matters. **David:** Before we wrap, is there anything we haven't covered that you think is important for us to understand? **Paul:** Just this: we're not anti-technology. We want better visibility. But we're also battle-tested on failed implementations. The difference between a successful platform and a failed one is usually whether the organization was really ready and whether the vendor understood our specific context. I've got confidence you guys are trying to understand our context, so that's a good start. **Sarah:** We'll get you that proposal this week. And we'll include some customer examples that are more directly applicable to your business. **Paul:** Great. And when you send it, maybe include a section on what typically happens if we try to do this and it doesn't work. Worst-case scenario. I'm the guy who has to explain it to the board, so I want to understand the risk. **David:** Fair point. We'll include that. **Sarah:** Thanks again, Paul. Really valuable conversation. Let's talk soon. **Paul:** Thanks, you two. I'm looking forward to seeing the proposal. --- ## Key Takeaways & Insights ### 1. **Vendor Consolidation is a Systems Problem, Not a Tools Problem** - Paul has four point solutions (Salesforce, Outreach, Gong, custom forecasting) but lacks integrated visibility - The pain isn't tool density; it's data fragmentation causing manual workarounds (spreadsheets) - He's explicitly looking for a "best-of-breed partner who specializes in sales execution" rather than layering more onto Salesforce - **Sales Implication:** Position as a specialized replacement/integration layer, not an add-on ### 2. **Budget Competing Against Retail Media Creates a Measurement Imperative** - Retail media has direct ROI measurement; sales platforms don't - Paul needs to prove that a sales execution platform can compete for CFO funding - Without baseline measurement, he can't build the business case - **Sales Implication:** First deliverable should be baseline analysis and quick-win ROI modeling (cycle time compression) ### 3. **Enterprise CPG Sales Cycles Require Deal-Type-Aware Forecasting** - Paul's customers range from 6-week deals (DTC) to 14-month deals (enterprise retail) - One standardized stage definition breaks down when deal types have fundamentally different timelines - Current spreadsheet approach adapts to this but creates visibility gaps - **Sales Implication:** Must demonstrate that the system can handle multiple deal types/buyer constellations without forcing a one-size-fits-all pipeline ### 4. **Change Management Will Require Executive Sponsorship + Pilot Success** - Reps default to spreadsheets/email when given options; forcing adoption requires CEO/CFO backing - 80-rep organization needs dedicated change management resources - Pilot approach (one region, 60-90 days) is the right entry path - **Sales Implication:** Make pilot success criteria explicit and achievable; position as low-risk proof of concept ### 5. **Quick Wins Around Cycle Time & Forecast Accuracy Are Highest Leverage** - One month of cycle time compression = $4-5M ARR impact (easily boardable metric) - Baseline measurement doesn't exist yet; Paul acknowledges this gap as embarrassing - Forecast accuracy (currently within 15-20%, goal is 5%) is another material metric - **Sales Implication:** Lead with "Here's your current baseline" analysis; make the forecast accuracy and cycle time case first ### 6. **Risk Acknowledgment Builds Trust in Enterprise Contexts** - Paul explicitly asked for a "worst-case scenario" section in the proposal - He's been burned before on failed implementations - Transparency about risk and failure modes differentiated the conversation - **Sales Implication:** Include risk/mitigation section in proposal; acknowledge historical IT failures and how this avoids them --- ## Conversation Dynamic Notes **Tone & Credibility Signals:** - Paul was skeptical but engaged once Sarah and David asked thoughtful questions - His repeated refrain about "being embarrassed" about not knowing metrics signals opportunity to fill that gap - When David asked clarifying questions (rather than pitching), Paul opened up more **Key Friction Points:** - Budget allocation (retail media vs. sales ops) is structural, not just preference - Rep adoption will be hardest obstacle; needs exec sponsorship to overcome - Baseline measurement paradox: he knows he needs it but hasn't invested in capturing it **Opportunity Indicators:** - He's already thinking about a pilot (West Coast region) before any proposal - He's given a clear timeline (CFO conversation late January, pilot decision by May) - He's willing to dedicate internal resources (60% of ops person) - He's open to implementation support and methodology training **Next Steps Readiness:** - Proposal scope is clear: baseline analysis, pilot scope, success criteria, timeline, cost, references - He wants worst-case scenario included - Executive alignment likely possible if pilot model is presented correctly - Timeline is realistic and aligned with budget cycles