Salesloft MCP Demo Server

# Interview: Michael Thompson - FinTech CRO ## Metadata | Field | Value | |-------|-------| | **Date** | January 10, 2026 | | **Duration** | 30 minutes | | **Interviewer** | Sarah Chen, Enterprise Solutions Manager, Salesloft + Clari | | **Interviewee** | Michael Thompson, Chief Revenue Officer, Apex Financial Technologies | | **Company** | Apex Financial Technologies (FinTech, $350M ARR) | | **Context** | Discovery call for compliance-driven sales acceleration platform | --- ## Conversation Transcript **[SALESLOFT REP]** Sarah Chen: Michael, thanks so much for taking the time today. I know you're incredibly busy running revenue for Apex. Before we jump in, I'd love to understand your biggest pain point right now. What's keeping you up at night when it comes to deal velocity? **[MICHAEL]** Michael Thompson: Sarah, honestly? Compliance. I know that sounds like a finance problem, not a sales problem, but it's become our biggest deal friction. We're closing deals slower than we should be, and it's almost always because of regulatory and legal bottlenecks. Last quarter, we had three deals that should have closed in Q3 that didn't close until Q4. That's millions of dollars on the table. **[SALESLOFT REP]** Sarah Chen: That's a really important insight, and I hear this from a lot of financial services companies. Can you walk me through what that actually looks like? When you say a compliance bottleneck, what's the real timeline impact? **[MICHAEL]** Michael Thompson: Sure. So let's take a real example. We had a deal with a regional bank—$2.3M contract. Sales team thought it was a 45-day sales cycle. That was optimistic. The client's compliance team got involved in week three, which pushed us into discovery mode for what their regulatory requirements were. We weren't equipped to speak to that early. Our reps had to keep looping in our head of compliance, which slowed everything down. **[SALESLOFT REP]** Sarah Chen: When did the legal team actually get involved? **[MICHAEL]** Michael Thompson: Not until week five or six. That's the real problem. By then, we'd already spent three weeks going in circles with the prospect's compliance officer, who kept saying "we need to confirm this meets our regulatory framework." Our legal team didn't start reviewing the contract until then. The whole thing stretched to 127 days instead of 45. **[SALESLOFT REP]** Sarah Chen: That's more than triple. And that's the deal cycle extension you're experiencing. How many of your deals are hitting this kind of compliance involvement? **[MICHAEL]** Michael Thompson: That's what keeps me up at night. I'd say roughly 60% of our enterprise deals now have a compliance component. Five years ago, it was maybe 25%. The regulatory environment has tightened significantly. Every financial institution we're selling to is more cautious about third-party vendor relationships. Our solution touches their customer data, so they're running SOC 2 audits, OFAC screenings, everything. **[SALESLOFT REP]** Sarah Chen: So compliance isn't just a legal checkbox—it's actually a qualification criteria for your deals now. How are your reps currently handling that? **[MICHAEL]** Michael Thompson: Not well, to be honest. We have maybe three people who understand the compliance landscape well enough to have early conversations. The rest of the team doesn't know what to ask for or when to escalate. I had a rep last quarter quote a 30-day implementation timeline without realizing our client's compliance framework required quarterly reviews. That pushed the whole deal three months out, and the rep didn't even flag it to leadership until we were already in the contract review stage. **[SALESLOFT REP]** Sarah Chen: That sounds like a knowledge and visibility gap. Are you seeing reps lose deals because they don't have that context upfront? **[MICHAEL]** Michael Thompson: Absolutely. We've lost at least two deals in the last six months because our reps didn't surface compliance concerns early enough. By the time legal got involved, the prospect had already moved us to a lower priority because they assumed our process wasn't aligned with theirs. One deal, the prospect just said, "We need a vendor that understands our regulatory environment better." **[SALESLOFT REP]** Sarah Chen: Ouch. So there's a qualification component, a deal structuring component, and a visibility component. Let me ask about this differently: If you could predict upfront which deals were going to have extended compliance cycles, would that change how you structure your sales process? **[MICHAEL]** Michael Thompson: Completely. We'd assign different reps. We'd bring legal in earlier. We'd have different discovery conversations. Right now, we're treating every deal like it's a standard technology sale, and compliance just... happens to us. If we knew a deal was going to require a parallel legal workstream, we'd approach it differently from day one. **[SALESLOFT REP]** Sarah Chen: What would that look like? **[MICHAEL]** Michael Thompson: First, we'd have a three-track approach. Sales track, compliance track, and implementation track running in parallel instead of sequentially. Right now, everything waits for legal to review the contract. But compliance can be validated independently. The prospect's compliance team can review our security framework while legal is reviewing payment terms. They're different conversations. **[SALESLOFT REP]** Sarah Chen: That makes total sense. And that requires knowing upfront which deals are high-compliance risk. How would you identify that? **[MICHAEL]** Michael Thompson: Good question. I think it starts with industry. Banks are 95% high-compliance. Insurance companies are about 75%. Fintech is maybe 40%. But within those, company size matters. A $100M FinTech is probably high-compliance. A $5M FinTech might not be. Regulated vs. unregulated. Whether they've been through vendor audits before. If they mention "compliance" or "regulatory" in early conversations, that's a huge signal. **[SALESLOFT REP]** Sarah Chen: So qualification criteria around compliance maturity and regulatory posture could flag deals early. What about stage definitions? Are your stage gates accounting for compliance complexity? **[MICHAEL]** Michael Thompson: No, that's actually a big gap. Our sales stages are pretty standard. Discovery, needs analysis, proposal, negotiation, contract. But what we're missing is a compliance validation stage. We should probably have a stage that's specifically "compliance assessment" or something that captures whether the prospect has identified regulatory blockers. Right now, deals can sit in negotiation for months because nobody's explicitly tracking compliance status. **[SALESLOFT REP]** Sarah Chen: So if you added that, and you could see which deals had legal escalations or compliance concerns flagged, would that change your probability calculations? **[MICHAEL]** Michael Thompson: Absolutely. We'd have a much more realistic deal forecast. Right now, I'm marking deals as 80% in negotiation, but 40% of those actually have unresolved compliance questions. The reps don't know it's a blocker. They think it's just taking longer. **[SALESLOFT REP]** Sarah Chen: That's the visibility problem. Let me shift to something else I'm hearing. You mentioned reps not knowing how to escalate or when to involve legal. How's your team's overall stability? Are you seeing turnover? **[MICHAEL]** Michael Thompson: Oh, we have a 32% turnover rate. That's our biggest people problem. And it's becoming a revenue problem. **[SALESLOFT REP]** Sarah Chen: What's driving that? **[MICHAEL]** Michael Thompson: A lot of things. Comp pressure—everyone's paying more for talent. But honestly, the bigger issue is ramp time. We're losing people right when they're getting productive. Our onboarding program is eight weeks, and it takes probably another 12-16 weeks before a rep is hitting full quota. So we're talking six months before someone is fully productive. And we're losing people in months three through six. They get frustrated because they're not hitting numbers. We're frustrated because we've invested in them and they haven't delivered yet. **[SALESLOFT REP]** Sarah Chen: What's their frustration based on? **[MICHAEL]** Michael Thompson: Lack of support, honestly. Our training is pretty generic. It's product features, demo, your territory. But there's no contextual training on compliance dynamics. New reps are jumping into calls where they should know to ask about regulatory requirements, and they don't. They lose credibility. A few months in, they've lost three or four deals, they're not hitting quota, and they leave. **[SALESLOFT REP]** Sarah Chen: So training and mentorship could actually impact retention? **[MICHAEL]** Michael Thompson: Dramatically. We have two reps who are killing it, and you know what? They both worked in financial services before sales. They understand the compliance angle instinctively. Everyone else is learning it the hard way. We've tried to create a mentorship program, but it's not structured. The top reps are too busy selling to effectively mentor. So new people struggle. **[SALESLOFT REP]** Sarah Chen: That's interesting because mentorship could be both a retention lever and a revenue accelerator. Speaking of leverage—I want to ask about mid-deal rep departures. That sounds like it could be a nightmare in a compliance-heavy environment. **[MICHAEL]** Michael Thompson: It's absolutely a nightmare. This is where the pain gets really real. We had this happen last quarter. One of our top reps, great guy, got recruited away by a competitor. He had three deals in flight—a $1.8M deal, a $900K deal, and a $600K deal. Total $3.3M pipeline. **[SALESLOFT REP]** Sarah Chen: Oh wow. What happened? **[MICHAEL]** Michael Thompson: Chaos. We had to transition those relationships to his replacement. But here's the thing—in deals with compliance components, the rep is usually pretty deep in the relationship. They've been on multiple calls with the prospect's legal team. They've been in discussions with compliance. When a new rep shows up, even if they're great, it feels like a disruption to the prospect. **[SALESLOFT REP]** Sarah Chen: Did you lose any of those deals? **[MICHAEL]** Michael Thompson: We didn't lose them completely, but we lost acceleration. Two of the three deals got pushed out by 30-45 days because the new rep had to ramp on the relationship. They didn't have context on what the prospect's compliance concerns were, what we'd already committed to, what the sticking points were. The prospect had to re-explain everything. It was inefficient. **[SALESLOFT REP]** Sarah Chen: And in a compliance scenario, that ramp time is probably longer because the new rep has to understand the regulatory nuances. **[MICHAEL]** Michael Thompson: Exactly. The first rep knew that this particular prospect was particularly concerned about GDPR compliance because they have European customers. New rep didn't know that. So in the first call, the prospect had to explain the whole business context again. It set us back. **[SALESLOFT REP]** Sarah Chen: How are you currently handling handoffs? **[MICHAEL]** Michael Thompson: Not great. Usually it's just a Slack message. "Hey, I'm leaving. Here are my accounts." There's no formal handoff process. Sometimes the outgoing rep will do a transition call. Sometimes not. The CRM has some information, but it's inconsistent. Some reps are religious about updating notes. Some are terrible at it. **[SALESLOFT REP]** Sarah Chen: So a rep could leave and the incoming rep doesn't have a full picture of deal status? **[MICHAEL]** Michael Thompson: Absolutely. I had a rep update a deal stage without explaining why. New rep took over and thought the deal was further along than it was. They didn't update the prospect on action items, missed a deadline the prospect was expecting, and the deal went cold. Those CRM hygiene issues are killer. **[SALESLOFT REP]** Sarah Chen: That's a relationship continuity problem. In a compliance-heavy deal, continuity is probably even more critical, right? Because the prospect has started a relationship with the first rep around compliance? **[MICHAEL]** Michael Thompson: 100%. When a legal team is involved, they're building a relationship with the sales rep. When that person leaves, it feels like a risk to them. They've shared sensitive information about their compliance framework, their concerns. A new rep has to rebuild that trust. And in the financial services world, trust is everything. **[SALESLOFT REP]** Sarah Chen: Let me ask a different angle. Are you tracking contract review timelines at all? **[MICHAEL]** Michael Thompson: Not really. Our finance team has a contract management system, but it's not integrated with sales. So I don't have visibility into when legal started reviewing a contract, when there are open issues, when it's back with the prospect. Sales reps are asking our legal team, "When will this be done?" and our legal team is saying "I don't know where this sits in your CRM," and there's just friction. **[SALESLOFT REP]** Sarah Chen: And that's a deal velocity killer because nobody knows the actual blockers. Legal could have an open question that kills the deal, but sales doesn't know about it. **[MICHAEL]** Michael Thompson: Exactly. Last quarter, legal had an escalation with a prospect about data handling. It went to their legal team. But our sales rep didn't know there was an escalation. So the rep kept pushing for a close date, and it made us look bad because we weren't aligned with their legal concerns. If I'd known there was an open legal issue, I would've told the rep to back off and give legal space to work it out. **[SALESLOFT REP]** Sarah Chen: That's interesting. So you need visibility into legal escalations so you can actually coach your reps on what to do—which is often to give space, not to push. **[MICHAEL]** Michael Thompson: Exactly. We're actually better served by reps knowing when not to push. The worst thing we can do in a compliance deal is bulldoze the prospect. That kills the relationship. **[SALESLOFT REP]** Sarah Chen: I want to go back to something you said earlier—"standard terms acceptance." How long does it take to get a prospect to accept your standard terms? **[MICHAEL]** Michael Thompson: Oh, it's a nightmare. Our legal team has standard terms, but hardly any prospect accepts them as-is. Most financial services clients come back with a list of changes. They want specific security requirements. They want specific data handling provisions. They want specific OFAC compliance language. Our legal team negotiates with their legal team, and it can take weeks. **[SALESLOFT REP]** Sarah Chen: Is that visibility gap again—does sales know what changes are being negotiated? **[MICHAEL]** Michael Thompson: Not usually. Our legal team operates pretty independently. There might be some major change that affects pricing or scope, and sales doesn't know about it until late in the process. I've had reps commit to a pricing model, then legal comes back with a request that requires custom work, and suddenly the deal margins are different. The rep doesn't know. **[SALESLOFT REP]** Sarah Chen: So there's a sales-legal integration problem. What would ideal look like to you? **[MICHAEL]** Michael Thompson: Sales and legal should be in sync from the beginning. If a rep qualifies a deal as "high-compliance," legal should be looped in early. Not just when the contract is ready to draft, but in discovery. Legal should understand what the prospect is worried about. Then when the contract comes up, there are no surprises. And sales should know what changes legal is negotiating so they can manage expectations with the prospect. **[SALESLOFT REP]** Sarah Chen: That requires earlier legal involvement. Is your legal team open to that? **[MICHAEL]** Michael Thompson: They're open to it in theory. But they don't have capacity. We have one general counsel and one legal coordinator. They can't be on every early discovery call. But maybe they don't need to be. Maybe they need to be on calls where we've already identified compliance as a likely issue. **[SALESLOFT REP]** Sarah Chen: That's where that qualification and prediction piece comes in. If you could flag high-compliance deals early, you could get legal involved in a smart way, at the right time, not trying to do everything. **[MICHAEL]** Michael Thompson: Exactly. And that ties back to training and rep knowledge. If reps knew what to look for, they could flag it. Right now, they don't even know what they don't know. **[SALESLOFT REP]** Sarah Chen: Let me ask about patterns. In the deals that have extended timelines, are there common characteristics? Beyond compliance? **[MICHAEL]** Michael Thompson: Yeah, actually. Company size is one. We're better at closing smaller accounts quickly. Larger deals—over $2M—almost always have compliance involved. Geographic location too. If a prospect has operations in Europe or Asia, compliance is guaranteed to come up. And interestingly, whether they've implemented a solution like ours before. If they have, it's usually a faster deal because they understand the security implications. If they're new to the category, it takes longer. **[SALESLOFT REP]** Sarah Chen: So those could be predictive indicators. And if you could identify those patterns early in the funnel, you could adjust your approach? **[MICHAEL]** Michael Thompson: We should, but we're not. We're treating every deal the same. And the deals where we need a different approach are the ones where that approach is most important. **[SALESLOFT REP]** Sarah Chen: Back to the rep turnover for a second. You mentioned a 32% turnover rate. If you could reduce that to, say, 20%, what would that mean for revenue? **[MICHAEL]** Michael Thompson: That's a 12-percentage-point improvement. On a 15-person team, that's basically keeping one more person productive per year. If an average rep generates $800K in revenue, that's $800K in incremental revenue. Plus you avoid ramp time on a replacement, plus you keep relationships continuity. It probably nets out to $1M+ in value. For a $350M ARR company, it's not everything, but it's significant. And that's just the direct revenue impact. There's also team morale. When you lose good people, the remaining team gets frustrated. They work harder to cover. It's exhausting. **[SALESLOFT REP]** Sarah Chen: So retention is a lever you want to pull. And part of that is supporting reps through the ramp period. What would better ramp support look like? **[MICHAEL]** Michael Thompson: Clearer expectations. Better training on the context they need—including compliance. Structured mentorship. Maybe assigning new reps to accounts that are less complex initially. Easier access to subject matter experts when they hit problems. And honestly, I think a CRM system that gives them visibility into what past deals look like would help. If a new rep could look at a closed deal and see the full journey—discovery notes, legal issues, what changed in negotiation—they'd learn faster. **[SALESLOFT REP]** Sarah Chen: That's institutional knowledge. Right now, that knowledge lives in people's heads? **[MICHAEL]** Michael Thompson: Mostly. Our best reps know all the patterns. New reps don't have access to that until they've been here six months. **[SALESLOFT REP]** Sarah Chen: Okay, last thing. If I told you we could build a solution that surfaced compliance risk early, that gave you visibility into legal bottlenecks, that helped you structure parallel workstreams, and that actually improved rep training through better deal data—would that be interesting to you? **[MICHAEL]** Michael Thompson: Extremely. Look, we love Salesloft. We've got them in. But where we're missing something is the integration with the reality of our sales environment, which is compliance-driven. And we need help with rep quality, ramp, and retention. If something could address all three, I'd be very interested. **[SALESLOFT REP]** Sarah Chen: I appreciate that. I think we might have something. But I want to understand your priorities. If you could only address one thing—deal velocity, rep retention, or deal visibility—what would it be? **[MICHAEL]** Michael Thompson: Deal velocity. That's the top-line number. But it's really all connected. Better rep retention means experienced reps handling complex deals, which accelerates velocity. Better deal visibility means better management, which helps with retention. It's all one system. But if I have to prioritize, it's velocity. A 30-day reduction in average deal cycle for $2M+ deals is worth millions. **[SALESLOFT REP]** Sarah Chen: That's fair. Let me take this back to the team. I'm going to have our product team dive into the compliance prediction angle and the legal integration piece. Can we set up another call in two weeks? **[MICHAEL]** Michael Thompson: Absolutely. And Sarah, appreciate the conversation. You actually asked the right questions. Most vendors come to us pitching features. You came to understand our business. That's refreshing. **[SALESLOFT REP]** Sarah Chen: That's what we're here for. Thanks, Michael. Really valuable insight. --- ## Key Takeaways ### Deal Dynamics & Compliance Impact - **60% of enterprise deals** now involve compliance components (up from 25% five years ago) - **127-day average cycle** on high-compliance deals (vs. 45-day target) - Compliance is a **qualification criteria**, not a late-stage gate - Three deals lost due to lack of compliance readiness ### Process & Visibility Gaps - No formal parallel workstream structure (compliance, legal, sales running sequentially) - Missing compliance validation stage in sales pipeline - Legal escalations invisible to sales team - Contract review timelines not tracked in CRM - Standard terms negotiation can extend 2-4 weeks with minimal visibility ### Rep Knowledge & Retention - **32% turnover rate** with peak attrition in months 3-6 after hire - Ramp time: 8 weeks training + 12-16 weeks to full quota productivity - Only 3 of 15 reps have financial services/compliance background - Mentorship program exists but lacks structure and capacity - New hire productivity loss: $1M+ annually due to attrition ### Relationship Continuity Issues - Mid-deal rep departures causing 30-45 day deal delays - Handoff process: informal Slack + inconsistent CRM notes - Prospects must re-explain compliance context with new rep - New reps lack historical deal context for learning ### Qualified Leads for Compliance-Focused Solution - **Strong interest** in early compliance risk identification - Need for legal-sales integration and coordination - Deal visibility and predictability as revenue lever - Rep training and institutional knowledge capture - High priority on deal velocity (primary metric) ### Predictive Indicators Identified - **Deal size**: $2M+ heavily correlated with compliance - **Geography**: European/Asian operations = guaranteed compliance - **Industry experience**: First-time category buyers slower than experienced prospects - **Company size**: Enterprise accounts more regulatory-intense --- *Interview conducted as part of discovery for compliance-driven sales acceleration platform. Follow-up scheduled in two weeks.*