# Interview: Thomas Anderson - Banking Technology CRO
**Date:** January 15, 2026
**Duration:** 32 minutes
**Interviewer:** Michael Chen, Enterprise Sales Manager, Salesloft
**Interviewee:** Thomas Anderson, Chief Revenue Officer, Banking Technology Solutions Inc.
**Company ARR:** $320M
**Industry:** Financial Services Technology
**Interview Type:** Discovery & Needs Assessment
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## Conversation Transcript
[SALESLOFT REP] Thomas, thank you so much for taking the time this morning. I know you're incredibly busy. Before we dive into anything specific, I'm curious—what does a typical week look like for you in the CRO seat at BTS?
[THOMAS] Ha, well, that's a loaded question. You know, it's a combination of things. I've got my finger in executive relationships—that's board reporting, quarterly reviews with our top customers who represent about 40% of our revenue. I'm also deeply involved in our product strategy, making sure that what we're building aligns with where the market's headed. But probably the biggest chunk is sales leadership and coaching. We have seven sales directors reporting to me, and I spend a lot of time making sure they're set up for success.
[SALESLOFT REP] That's helpful context. And when you think about your sales organization, where do you feel the biggest friction points are right now?
[THOMAS] Oh, there are several. The first is forecasting accuracy. We sell to banks and financial institutions, and the sales cycles are absolutely brutal. We're typically looking at 18 to 24 months from first conversation to signature. Some deals, especially the really large ones, can stretch to three years. That creates this enormous pipeline management challenge because you have so much in flight, and the risk of things slipping is high.
[SALESLOFT REP] 18 to 24 months—that's not unusual for financial services, but that's still a long time to manage. Walk me through what that cycle typically looks like.
[THOMAS] Sure. So we usually start with a discovery phase, maybe two to three months. That's us understanding their current state, their pain points, their existing technology stack. It's mostly conversations with the CIO's office—the CIO, the VP of Technology, maybe some architects. Once they're comfortable with what we're solving for, it moves to what we call the "scoping and design" phase. That's another three to four months, sometimes longer. This is where we're working with their team to design the solution, understand the integration requirements, and really nail down what success looks like.
[SALESLOFT REP] And during that phase, are there gatekeepers or approvers you're dealing with beyond the CIO?
[THOMAS] Absolutely. The CIO is critical, but they're not the only person. We're also talking to the CFO or the VP of Finance because there are budget implications. We're talking to the Chief Compliance Officer or their GRC team because this is financial services—compliance is baked into everything we do. And increasingly, we're talking to the Chief Risk Officer. And of course, depending on what we're selling, we might need buy-in from business unit heads—if we're selling something to the wholesale banking division, we need the head of that business.
[SALESLOFT REP] So you're not just selling to the CIO. The CIO relationship is almost like a champion or a necessary ally, but—
[THOMAS] Right, exactly. The CIO relationship is absolutely critical, but here's the thing—it's not primarily about the product anymore. I mean, yes, the product needs to be good. But at the CIO level, what they care about is strategy. Can you help us modernize? Can you help us reduce technical debt? Can you help us free up resources from managing legacy systems so we can focus on building competitive advantages? The CIO is a strategist first, a technologist second.
[SALESLOFT REP] That's a really important distinction. How does that change your go-to-market?
[THOMAS] It changes everything, frankly. It means I can't send a sales engineer in with a PowerPoint about features and expect to win. What I need to do is come in with market intelligence. What are other banks doing? What's the regulatory environment looking like? What are the industry trends? The CIO wants to be strategic, and we need to be a partner in that strategic thinking. That's why my AEs spend a lot of time on business acumen, not just product acumen.
[SALESLOFT REP] Let's stay with that. You mentioned regulatory environment. How much is that shifting your pitch or your customers' priorities?
[THOMAS] A lot, actually. In the past 18 months, we've seen major regulatory changes around data residency, open banking regulations—things like PSD2 in Europe, but also equivalents emerging elsewhere. There's also been a lot more scrutiny on AI and algorithmic bias in financial services. These regulations aren't being enforced yet, but banks are panicking. They know they need to be ready in 12 to 18 months, and they're starting to budget for it now. So a lot of our conversations that were purely about modernization or efficiency are now including a compliance or risk management angle.
[SALESLOFT REP] How far in advance are banks typically thinking about this?
[THOMAS] Honestly, it varies. The really mature banks are thinking 18 to 24 months out. They have compliance teams that are monitoring regulatory bodies and drafting internal policies. But a lot of mid-sized banks are reacting more than anticipating. They're getting surprised by change more often. For us, it means we need to be the ones bringing the intelligence. We need to have a point of view on where regulation is headed and how our solution helps them get there.
[SALESLOFT REP] So market intelligence is almost a sales enablement tool for you—
[THOMAS] Completely. It's one of the biggest gaps I see in my own sales organization, actually. My AEs are good at talking about what our product does. They're less comfortable talking about the broader market trends and helping customers understand how those trends affect their business. That's something we're actively trying to improve.
[SALESLOFT REP] Let me pivot a bit. You mentioned the 18 to 24-month cycle. How do you manage pipeline visibility through that? How do you know which deals are actually likely to close?
[THOMAS] That's where a lot of my frustration comes in. We have a CRM—Salesforce—but honestly, the way we're using it today, I can't tell the difference between a deal that's genuinely progressing and a deal that's stuck. A sales rep will tell me, "We're in design phase," but I don't actually know if they've had a meeting in the past two weeks or if they're just hoping for the best.
[SALESLOFT REP] How are you currently trying to address that?
[THOMAS] We've implemented quarterly business reviews with each of our sales directors. We pull the Salesforce data, and we go through the pipeline deal by deal. But it's manual, it's time-consuming, and frankly, by the time we're identifying a deal that's stuck, we're already three or four months behind where we could have been proactive. What I really need is visibility in real time into which deals are moving, which ones have stalled, what the actual engagement looks like. Are the right people talking to the right people? Is there genuine consensus from the customer side?
[SALESLOFT REP] What would change if you had that visibility?
[THOMAS] Everything. First, I could reallocate resources. If I see a deal that's stuck in design phase because the customer's internal team is disorganized, I could send in one of my senior AEs or my VP of Sales to help facilitate. Second, I could forecast more accurately for the board. Right now, I'm forecasting based on gut feel and historical probability. I'll say, "Okay, this bucket of deals is 40% likely to close in Q2 based on the fact that we closed 40% of deals in this phase in the past." But that's pretty crude. If I actually knew which deals had momentum and which ones didn't, I could forecast with much more confidence. Third, I could manage my sales team differently. I could see who's actually engaged and who's just grinding it out.
[SALESLOFT REP] That makes sense. Let me ask about stage definitions then. When you say "design phase" or when your reps say it, how consistent is that definition across your team?
[THOMAS] Eh, that's a problem. I have one director who defines "design phase" as "they've committed to having a design meeting." I have another who defines it as "they've completed the design and agreed to it." Obviously, those are very different things in terms of probability. So yeah, stage definitions are pretty loose.
[SALESLOFT REP] Have you tried to tighten those up?
[THOMAS] We've tried. Sales orgs hate being told they're wrong, even by their own VP. We put together stage definitions a couple years ago, but they kind of drifted over time. And honestly, when you're dealing with cycles this long, the stages get fuzzy. You might think you're in "decision phase" but actually the customer's got three more internal approvals they haven't told you about.
[SALESLOFT REP] So the customer isn't always transparent about where they actually are in their buying process.
[THOMAS] Correct. And that's partly because they themselves don't always know. They might have a procurement department working on vendor selection, a technical team evaluating the solution, a compliance team doing their own assessment, and a finance team looking at pricing. These teams might not be talking to each other, so the customer-facing contact might tell you they're ready to move forward, but actually there's a compliance hold you don't know about.
[SALESLOFT REP] That's interesting. So the customer isn't being evasive intentionally; they're just compartmentalized.
[THOMAS] Exactly. The organizations we sell to are just really complex. And in a 24-month cycle, there's so much risk of things falling apart. People leave. Priorities change. New executives come in and want to revisit decisions. We had a deal last year that was 22 months in—we'd negotiated terms, we were on contract review—and the customer's CIO got promoted. The new CIO wanted to do their own evaluation, which meant we had to start over with the evaluation phase.
[SALESLOFT REP] That's painful.
[THOMAS] It was a $2.5 million deal. We're talking about a deal that was probably going to close in Q4, but because of an executive change, we're looking at Q2 of the following year. That's a six-month slip.
[SALESLOFT REP] How do you prevent that? How do you protect your deals from executive transitions?
[THOMAS] You build relationships broadly. You can't rely on a single champion, even a powerful one like the CIO. You need to make sure you have relationships with the CFO, the Chief Risk Officer, the head of the business unit. But honestly, that's harder for me as a CRO to cascade down to my team than it sounds. My AEs are naturally going to focus on whoever is the most engaged. If the CIO's office is moving things forward, that's where they'll spend their energy. Getting them to go broader requires a level of discipline that not everyone has.
[SALESLOFT REP] Let's talk about the vendor evaluation part of this. When a bank decides they need a solution like yours, how rigorous is their evaluation process?
[THOMAS] Extremely rigorous. There's usually an RFP, sometimes even multiple RFPs. They'll ask us to detail our integration approach, our security practices, our compliance certifications, our business continuity plans. Then they'll do a POC—a proof of concept—where we have to demonstrate that the solution works in their specific environment. And the POC is usually not trivial. It might be a two to three month engagement where we're working with their team to get real data loaded, run real processes, see if it works.
[SALESLOFT REP] How much of that work do you do before you've even negotiated terms?
[THOMAS] Oh, most of it. Probably 70 to 80% of the work is done in the evaluation phase, before we're even close to an agreement on pricing or contract terms. It's a significant investment.
[SALESLOFT REP] And that's just part of what they need to do before they can justify the investment to their board or their CFO.
[THOMAS] Right. And here's where it gets interesting—there's also a vendor risk assessment step. We have to complete the customer's vendor due diligence process. They want to understand our financial health. Are we going to be around in five years? They want to understand our regulatory status. Are we registered with the Fed? Are we compliant with all the relevant regulations? They want to understand our data security practices. What certifications do we have? How do we handle data? Where is data stored? For our largest customers, this can be a multi-month process on the customer side that has nothing to do with evaluating the product—it's just about whether they can do business with us at all.
[SALESLOFT REP] How early in the sales cycle does that vendor assessment start?
[THOMAS] That's the question. Ideally, they'd start it early so it doesn't become a blocker later. But a lot of customers don't start the vendor assessment until they're pretty convinced they want to buy. They'll say, "Let's get through the technical evaluation, and then we'll do vendor due diligence." But that's risky because vendor due diligence can take four to six months, and if there's an issue—if we can't meet one of their compliance requirements or if our financial position doesn't look solid—then you're looking at a restart.
[SALESLOFT REP] Have you had deals die in vendor due diligence?
[THOMAS] Not die exactly, but definitely extend. We had a customer who was ready to move forward, but their Chief Compliance Officer had a question about our data residency capabilities. We have data centers in the US, but they needed data to stay within the EU under PSD2. We told them we didn't have a solution for that yet, but we had it on the roadmap. They said, "Come back when it's live." So that deal moved from Q2 to Q4, maybe Q1 of the next year, depending on when we shipped that capability.
[SALESLOFT REP] That's important context. Now, let me ask about integration. You mentioned earlier that legacy system integration is always required. Tell me about that.
[THOMAS] Yeah, this is huge. Every bank we work with has legacy systems. They have mainframes running COBOL code that's 30, 40 years old. They have older packaged systems that were implemented 15, 20 years ago. They might be running on different databases, different platforms. When we come in with a new solution, we can't just plug it in. We have to integrate with all of this existing stuff. We have to pull data from multiple sources, transform it, load it into our system. And in financial services, that data has to be absolutely clean and accurate.
[SALESLOFT REP] How much does that integration piece drive the length of the cycle?
[THOMAS] Probably 30 to 40% of the cycle time. If they didn't have integration requirements, we could probably move from evaluation to implementation in three or four months. Because they do, it's more like six to nine months just for integration.
[SALESLOFT REP] And is that something your team discovers during the sales cycle, or do customers come in already knowing they need heavy integration?
[THOMAS] Both. Some customers, usually the sophisticated ones, they come in knowing they need integration. They'll tell us upfront, "We're going to need to integrate with our core banking system, our lending platform, and our data warehouse." Other customers, especially smaller banks, they underestimate it. They think, "Oh, you'll just connect to our API and pull the data." Then when we do discovery during the POC, we realize the APIs don't exist or they're incomplete or they're not documented. We end up having to do custom integration work.
[SALESLOFT REP] How do you price that?
[THOMAS] That's where it gets tricky. If it's heavy custom integration, we usually have two approaches. One is services—we have a consulting arm that can do the integration work, and we charge hourly or fixed-fee for that. The other is we'll price the software license higher and absorb some of the integration cost because we know it's a loss leader for us to get the customer live. We're betting that once they're live, they'll renew and expand.
[SALESLOFT REP] Is the integration work ever a deal-killer?
[THOMAS] Rarely, but sometimes. If the integration is way more complex than expected and the cost balloons, the customer might decide, "This is too much effort. We're going to stick with our current solution and upgrade our legacy system instead." That's happened to us a couple times.
[SALESLOFT REP] Let me come back to something you said about the CIO relationship. You said that the product isn't the primary selling point anymore—it's the strategic relationship. How do you translate that into your messaging?
[THOMAS] That's probably the biggest evolution in how we're going to market. Traditionally, our messaging was very product-focused: "We help banks modernize their core systems." Very feature-oriented. What we're shifting to is a more strategic narrative: "We help you solve for regulatory compliance, reduce technical debt, and free up your team to work on competitive advantages." It's the same product, but the value prop is positioned very differently.
[SALESLOFT REP] And how's that resonating?
[THOMAS] Honestly, it's early. We've piloted this messaging with a couple of directors and they're seeing better engagement at the CIO level. The conversation is richer. The CIO's actually interested in talking to us because they feel like we understand their strategic challenges, not just their technical problems.
[SALESLOFT REP] What kind of market intelligence are you using to support that?
[THOMAS] We subscribe to a couple research firms—Gartner, Forrester, IDC—and we pull their reports on digital transformation, modernization trends in banking. We track regulatory changes and what guidance the Fed is putting out. We monitor industry news and see what our customers are doing. For example, when SVB collapsed a few years ago, all our customers suddenly got very focused on risk management and operational resilience. We leveraged that to reframe our pitch around how our solution helps with operational resilience.
[SALESLOFT REP] So you're actively looking for those inflection points and then adjusting your messaging.
[THOMAS] Exactly. And the hardest part is getting my team to stay current on that. I'll share a Gartner report with my sales directors and expect them to digest it and use it to coach their teams. But they're busy, they're focused on closing deals, and it's not always top of mind. So we're thinking about how we can make this easier for them—maybe condensed briefings, maybe updated competitive intel, maybe just giving them better talking points.
[SALESLOFT REP] You've touched on this, but let me ask directly: How much does the CIO relationship matter relative to the buying process itself?
[THOMAS] The CIO is probably 60 to 70% of the decision, if I had to put a number on it. They have veto power. If the CIO says no, you're done. But they might say yes, and then the CFO says no because of pricing. Or they might say yes, and then compliance says no because of a regulatory issue. So it's not deterministic. But if you lose the CIO, you lose the deal.
[SALESLOFT REP] And how much of your sales process is specifically designed to win the CIO?
[THOMAS] Honestly, probably not enough. We have senior AEs and sales engineers, and they'll spend time with the CIO. But at some point, the CIO's going to want to talk to my VP of Sales or to me. They want to know that we're strategic partners and that there's real investment from the executive team. So I end up spending a lot of time on CIO relationships, especially for our largest deals.
[SALESLOFT REP] That's a huge time commitment.
[THOMAS] It is. And it's not scalable. I can handle maybe four or five strategic relationships at any given time. Beyond that, I'm not as present. So one thing we're thinking about is how we can better equip our team to handle those relationships without always needing an executive in the room.
[SALESLOFT REP] You mentioned the board earlier. How much of your CRO time is spent on board reporting and board management?
[THOMAS] A lot. Every quarter, I present to the board on our pipeline, our forecast, our progress toward our annual revenue targets. They want to understand our win/loss analysis, our churn, our expansion revenue. The board is very focused on predictability and growth, which makes sense for a $320M ARR company. So I spend a lot of time making sure that our forecasting is accurate and that we can explain any deviations. If I forecast a $10M deal and it slips, I need to be able to explain why it slipped and when it's going to close.
[SALESLOFT REP] How well can you do that today?
[THOMAS] That's one of the biggest pain points for me. I can tell the board where the money is—it's in the pipeline. But I can't always explain with certainty why something's not closing as expected. Is it a sales execution issue? Is it a product gap? Is it a timing issue on the customer side? Without that visibility, I'm kind of flying blind.
[SALESLOFT REP] I imagine that's creating pressure on your sales team to deliver.
[THOMAS] Absolutely. And that pressure filters down. Sales reps are feeling it. They're trying to move deals forward, but they might be moving a deal forward that's not actually ready. They might be pushing on a customer too early, which can damage the relationship. So there's a balance between urgency and patience that we're constantly trying to strike.
[SALESLOFT REP] Let's talk about something else. In your experience, how much of the deal risk comes from the customer side versus the sales team side?
[THOMAS] That's a good question. I'd say it's probably 70% customer side, 30% sales side. On the customer side, you have organizational changes, priority shifts, budget constraints, compliance issues that pop up unexpectedly. On the sales side, you have execution issues—reps not following up, reps not qualifying opportunities early enough, reps not building relationships broadly. If I could reduce that 30% that's in my control, it would make a huge difference.
[SALESLOFT REP] What does execution look like for you? What does best-in-class look like?
[THOMAS] Best-in-class is an AE who is deeply engaged with the customer, who understands the customer's business, who has relationships at multiple levels, who is actively helping the customer solve problems, not just selling to them. The AE should know what's happening inside the account—what meetings are scheduled, who's engaged, where the deal is really at versus where it appears to be. The AE should be forecasting accurately, updating the CRM consistently, and escalating issues early rather than late.
[SALESLOFT REP] How consistent is that across your team?
[THOMAS] Not as consistent as I'd like. I have some AEs who are fantastic at this. They're the ones closing the biggest deals. But I have others who are, frankly, order-takers. They'll send a proposal to a customer and hope for the best, rather than actively managing the opportunity. Getting everyone to that best-in-class level is a constant challenge.
[SALESLOFT REP] Is there anything that would help you scale that behavior across the team?
[THOMAS] Coaching and visibility. I need my sales directors to be coaching more, and I need visibility into what's actually happening in the deals so I can see where coaching is needed. Right now, a lot of my coaching happens at the quarterly business reviews when it's already too late. I wish I could be more real-time about it.
[SALESLOFT REP] Let me ask you about something different. You mentioned compliance and regulatory changes. How much of an opportunity or threat is that for you?
[THOMAS] Huge opportunity. These regulatory changes are forcing every bank to reevaluate their systems and their processes. We're the solution that helps them do that. But it's also a threat because if we're not positioned right—if we're not understood to be compliant, if we're not helping them solve for regulatory requirements—then we lose to competitors or we lose to the customer's decision to upgrade their existing systems instead.
[SALESLOFT REP] How much is regulatory expertise baked into your sales motion?
[THOMAS] We have compliance specialists on the sales engineering team who get involved in conversations. And we have a consulting division that can help customers map their processes to compliance frameworks. But it's not seamless. A lot of times, we're reacting to a customer asking about compliance rather than proactively bringing it up. We're not leveraging the regulatory trends as much as we could.
[SALESLOFT REP] What would it look like if you were more proactive about it?
[THOMAS] I think it would look like sales conversations starting not with "What are your pain points with your current system?" but "Here's what's happening in the regulatory landscape, and here's how that affects your business over the next 18 to 24 months." We'd be the ones educating the customer on the trends and the implications. That's very different from where we are today.
[SALESLOFT REP] That requires a different level of sales acumen.
[THOMAS] It does. And it requires my team to stay current on things that change constantly. New regulations, new guidance from the Fed or other regulators. It's almost like we need a regulatory expert or a market intelligence person who's feeding information to the sales team on a regular basis.
[SALESLOFT REP] I want to come back to something you said about the CIO relationship being 60 to 70% of the decision. In a perfect world, how would your sales process be designed to manage that relationship?
[THOMAS] In a perfect world, we'd identify the CIO early. Actually, we'd identify them even before we have a conversation with the customer—we'd know who the CIO is, what their background is, what they're worried about. Then our first approach wouldn't be to the CIO directly; it would be to someone who has credibility with the CIO—maybe the CFO or the CEO. We'd position the CIO's strategic challenges, get some air cover from above, and then approach the CIO with a peer-level conversation. Our VP of Engineering or VP of Product would talk to the CIO about strategy, not a sales rep.
[SALESLOFT REP] So you'd almost have executive alignment before you have a sales conversation.
[THOMAS] Exactly. That's what the best deals feel like—it's not a sales cycle, it's a mutual exploration that leads to a decision. The executive sponsorship is already in place, the CIO is already engaged, the CFO is already thinking about it, and the sales team comes in to facilitate the rest of the process.
[SALESLOFT REP] How often does that happen for you?
[THOMAS] Rarely. Maybe 20% of the time. Most of the time, we're selling bottom-up or sideways. We get an introduction to someone in the organization, and we're trying to work our way up to the CIO or across to the CFO. It takes longer and it's messier.
[SALESLOFT REP] What would increase the percentage of top-down deals?
[THOMAS] Brand, primarily. If we were more well-known at the CIO level as a strategic thought leader, we'd get more inbound from CIOs. We'd also get more warm introductions from our existing customers or from advisors who know us. Right now, we're mostly doing cold outreach or working through our channel partners. That's not as effective.
[SALESLOFT REP] Let's talk about your sales team structure for a second. You mentioned seven sales directors. What does the organization look like?
[THOMAS] Seven directors, and under each director, there are probably three to five AEs. So we're looking at maybe 35 to 40 AEs total. They're organized by geography and by customer size. We have a team focused on the top 20 customers, a team focused on mid-market, and a team focused on smaller institutions. We also have sales engineers and a consulting division. Overall, probably 60 to 70 people in the revenue organization.
[SALESLOFT REP] How much is pipeline coverage as a multiple of your annual target?
[THOMAS] We're aiming for 3x. So if we have a $100M target, we want $300M in pipeline. We're not always there. Some quarters we're at 2.5x, which creates stress. It means we have to assume a higher conversion rate or we're going to miss our number.
[SALESLOFT REP] And what are your conversion rates looking like by stage?
[THOMAS] That's where it gets messy because our stage definitions are loose. If I'm honest, I don't have clean stage-to-stage conversion numbers. I have overall pipeline to close numbers, which is something like 15 to 20% on average, but that's a lagging indicator because of the long cycles.
[SALESLOFT REP] 15 to 20% seems pretty healthy for your space.
[THOMAS] It does, but I think it masks underlying issues. Some deals might be converting at 50%, some at 5%. Some stages are moving faster than they should be, which is a sign that we're not qualifying hard enough. Other stages are moving slower than they should be, which is a sign that we're stuck.
[SALESLOFT REP] If you could solve one problem with your sales process, what would it be?
[THOMAS] Honestly, it would be visibility and accuracy in forecasting. If I could forecast accurately three months out, I could manage the business so much better. I could know where to allocate resources, which deals need attention, which ones are healthy. Right now, I'm managing with a lot of uncertainty, and uncertainty creates anxiety and makes me feel like I'm not doing my job as well as I could.
[SALESLOFT REP] Michael, let me ask you something. When you think about tools or approaches that could help with that, what comes to mind?
[THOMAS] I mean, we have Salesforce, and we use it. But the tool is only as good as the data, right? So the issue isn't the tool; it's getting my team to keep the data clean and up-to-date and honest. Some reps are religious about updating Salesforce. Others... not so much. We've tried implementing sales ops rules—like you can't forecast a deal until you've logged a certain number of activities. But it feels heavy-handed and it doesn't really solve the underlying problem, which is that my team doesn't have a unified way of thinking about what stage means or what activities matter.
[SALESLOFT REP] So you need alignment around what good looks like.
[THOMAS] Yes. And then you need visibility into whether people are actually doing it. And then you need coaching to help people get better.
[SALESLOFT REP] Let me ask a different question. Your customers are going through these long cycles, 18 to 24 months. How much are they struggling with that as well? How much is that a frustration for them?
[THOMAS] Oh, absolutely. Especially for their procurement teams. The procurement director at a bank is under pressure to get new vendors through quickly, but the other departments—IT, compliance, risk—are slow. So they're stuck in the middle. They want to move forward but they can't. And that frustration sometimes works in our favor because they want to figure out how to streamline the process. Sometimes it works against us because they give up.
[SALESLOFT REP] Do customers ever ask you how you can help them compress the cycle?
[THOMAS] Some do. We usually tell them we'll do pre-work on compliance and vendor assessment to get ahead of it, and we'll designate a senior person from our team to be available for questions and to facilitate internally. But honestly, we can only compress it so much. The customer's internal process is what it is. We can be responsive, but we can't make their compliance team move faster.
[SALESLOFT REP] What if there was a way to help them anticipate what they'd need to do during vendor assessment before the process officially starts?
[THOMAS] That would be valuable. If we could give them a checklist or a framework that said, "Here's what we know you're going to ask for as part of vendor due diligence, and here's what we have prepared," that would help them move faster because they'd know what to expect.
[SALESLOFT REP] Do you do that today?
[THOMAS] We have some materials—a security overview, a compliance overview, business continuity documents. But it's not systematized. It's just documents scattered around. It would be better if there was a structured process where we're proactively sharing information and pre-answering questions.
[SALESLOFT REP] Last question. If I were to come back and show you how we could help you with visibility, pipeline management, and coaching your team, would that be interesting to you?
[THOMAS] Absolutely. The caveat is it has to be easy to implement and it can't create more work for my team. We're already stretched thin. But if it's something that helps us see what's really happening in the deals and helps my directors coach better, I'm all ears.
[SALESLOFT REP] Perfect. I appreciate your time, Thomas. This has been really helpful.
[THOMAS] Happy to help. Feel free to reach out anytime. And send me that information when you have it.
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## Key Takeaways
### 1. **Extended Sales Cycles Are the Central Challenge**
Thomas emphasizes the 18-24 month procurement process as the defining characteristic of his business. The length of these cycles creates cascading challenges around forecasting, resource allocation, and deal hygiene. Executive changes mid-cycle and customer compartmentalization further complicate the journey.
### 2. **CIO Relationships Are Strategic, Not Transactional**
The CIO is the most critical stakeholder (60-70% of decision-making power), but the sale is based on strategic partnership and market understanding rather than product features. CIOs care about modernization, regulatory compliance, and competitive advantage—not technical specifications. This requires executives at the table, not just sales engineers.
### 3. **Regulatory Changes Are Both Opportunity and Threat**
Banking regulations (PSD2, data residency, algorithmic bias) are shifting customer priorities 18-24 months out. Customers need market intelligence and advisory guidance, not just products. Thomas is under-leveraging this competitive advantage in his messaging today.
### 4. **Legacy System Integration Drives 30-40% of Cycle Time**
Every customer has mainframe systems, older packaged solutions, and complex APIs. Discovery during POC often reveals integration needs worse than expected. This is a pricing and scope challenge—Thomas often absorbs integration costs to get deals across the finish line.
### 5. **Vendor Assessment Is Increasingly a Blocker**
Compliance teams, CROs, and procurement now conduct formal vendor due diligence separately from product evaluation (4-6 months). Early, proactive information sharing about security, compliance, and business continuity could reduce cycle time and prevent late-stage deal slips.
### 6. **Pipeline Visibility Is Critical but Lacking**
Stage definitions are loose, forecasting accuracy is ~15-20% (but masking variation by stage), and CRM data is only as good as rep discipline. Thomas needs real-time visibility into deal momentum and engagement to coach effectively and forecast accurately to the board.
### 7. **Executive Sponsorship Matters**
Top-down deals with CEO/board-level alignment close faster and more reliably. Only 20% of Thomas's deals are top-down today; most are bottom-up, requiring longer cycles and more sales execution. Brand and executive positioning would improve this ratio.
### 8. **Sales Team Coaching Is the Limiting Factor**
Thomas has strong AEs but inconsistent execution across the team. Coaching happens quarterly at best. Better visibility and real-time coaching could improve conversion rates and forecast accuracy without adding headcount.
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**Document Prepared By:** Michael Chen, Salesloft
**Follow-up Actions:** Schedule demo of pipeline visibility and coaching platform; prepare customer success case studies focused on cycle acceleration
