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# Interview: Nancy Chen - Mental Health Platform VP Sales ## Metadata **Date:** January 2, 2026 **Duration:** 32 minutes **Interviewer:** Marcus Thompson, Enterprise Sales Engineer, Salesloft + Clari **Interviewee:** Nancy Chen, VP Sales, MindWell Health (Mental Health Platform) **Company:** MindWell Health - $35M ARR, 150+ enterprise clients **Recording:** Zoom, transcript reviewed by interviewee --- ## Interview Transcript **[SALESLOFT REP]:** Nancy, thanks so much for taking the time this morning. I know you're incredibly busy ramping a new sales organization. Before we dive into anything, I'd love to just start with you telling me about what's happening at MindWell right now. How's the scaling going? **[NANCY]:** Thanks for having me, Marcus. Yeah, it's been... well, it's been a lot. We're at this really interesting inflection point. We've built something that clinically works—like, we have data—but selling it enterprise at scale has revealed some things we weren't really prepared for. We're at $35M ARR, which sounds great until you realize we're trying to go from selling to benefits consultants and HR partners to selling directly into enterprise accounts. The motion is completely different. **[SALESLOFT REP]:** I'm really curious about that transition. You've obviously been successful, but you're right—selling to enterprise is its own beast. What's the biggest gap you're seeing as you try to scale? **[NANCY]:** Honestly? Everything. We have a sales team that knows how to navigate the benefits consulting channel—that's been our bread and butter. But when you walk into a $10B company and you're sitting across from the VP of Total Rewards, they don't care that we have clinical outcomes. They want to know: one, is this going to blow up my benefits budget? Two, who else is buying this? And three, why should we trust you more than the 47 mental health apps already on our benefits platform? **[SALESLOFT REP]:** Let's tackle number one first because I think it's foundational. When you're talking to benefits leaders right now, what does that conversation around budget look like? **[NANCY]:** This is where it gets painful. Most companies have a line item for "mental health benefits" and it's... not growing. It's either flat or it's being cut. The conversation usually starts with the benefits leader or the Chief Health Officer saying, "We already have coverage for mental health through our EAP, our insurance, maybe we've got some employee assistance program." So their mental health spend is already allocated. What we're asking them to do is essentially reallocate budget—move money from those existing programs into us—and justify that to Finance. **[SALESLOFT REP]:** So you're not expanding a growing bucket, you're asking them to cannibalize. **[NANCY]:** Exactly. And the person who's championing our solution internally—usually an HR business partner or the benefits lead—they're not the ones who approved that original budget. Finance did. So they have to go back to Finance and say, "Hey, we want to spend less on the EAP and more on this clinical platform." Finance asks for ROI. And here's the problem: we have outcome data, but it's not in a language Finance speaks. We're talking about clinical remission rates, symptom improvement scores, things like that. Finance wants to know: what's the cost per member per month? How many employees will actually use this? What's the engagement rate? What's the impact on medical claims over a two-year period? **[SALESLOFT REP]:** Do you have that data? **[NANCY]:** We have some of it. We have engagement data, we have clinical data, but we don't have a robust model that shows the medical claims impact. And frankly, even if we did, the payback period is long. That's part of being clinical versus being a lifestyle app. We're not just making someone feel better in the short term. We're actually treating conditions, and that takes time. **[SALESLOFT REP]:** How much time are we talking about? **[NANCY]:** Three to five years to see meaningful medical claims reduction, maybe longer. Some conditions might take two years, some take longer. Depression, anxiety, we can show improvement in 8-12 weeks. But the impact on reduced medical costs, reduced absenteeism, increased productivity—that's a longer tail. We've done some studies showing the ROI by year three, but if you're asking a Finance leader to justify a budget reallocation on a three-year payoff... they're going to be skeptical. **[SALESLOFT REP]:** I imagine they're thinking about their tenure in that role, right? Most Finance leaders, VPs, they're thinking on a 12-18 month horizon. **[NANCY]:** Precisely. So we've started trying to use intermediate metrics. We talk about clinical improvement—people getting better faster means they're back to productivity sooner. We talk about medical claims trends. We reference case studies, and we try to make the case based on what our clients have already seen. But here's the honest truth: we're still new enough in the enterprise space that our track record is limited. Most of our success stories are in mid-market or with early adopter enterprises. We don't have a $100B Fortune 500 company saying "Yes, this saved us $5M in medical claims." And that's what would move the needle. **[SALESLOFT REP]:** So the credibility gap is real. They want to see a peer who's already done this at scale. **[NANCY]:** Completely. And because no one's done it yet—or if they have, they're not talking about it—we're stuck in this chicken-and-egg problem. We need the big client to move first, but the big client won't move until someone else has already moved. **[SALESLOFT REP]:** Let's talk about something else I'm hearing from mental health companies: privacy. How is that showing up in your conversations? **[NANCY]:** Oh man, it's huge. And it's gotten worse in the last six months. After the whole data privacy thing with [competitor] where their infrastructure was compromised, and then that story about the app that was selling location data to data brokers... enterprises are terrified. Mental health data is the most sensitive data they hold. It's more sensitive than anything—it reveals everything about a person. Their vulnerabilities, their family situation, their financial stress, their ability to function. So when we walk in and say, "Your employees can get clinical treatment through our platform," their first question is now: "Where does the data live? How is it encrypted? Who has access? What are your compliance certifications?" **[SALESLOFT REP]:** What are you telling them? **[NANCY]:** The truth, which is actually pretty good. We're HIPAA-compliant. We have SOC 2 Type II certification. All data is encrypted in transit and at rest. We never sell data, we never share data with third parties for marketing or research without explicit consent. Our therapists are licensed, our clinical protocols are published and peer-reviewed. But here's the issue: every other mental health app says the same thing. And some of them are lying or cutting corners. So just saying the right thing isn't enough. We have to earn trust. **[SALESLOFT REP]:** How are you trying to do that? **[NANCY]:** Security audits. We bring in third-party penetration testers, and we share the results with prospects. We're really transparent about our data retention policies—we delete data after a certain period unless the user consents otherwise. We have an ethics board that reviews our practices. And we're trying to build relationships with their legal and security teams early. The benefits leader cares about engagement metrics, but the Chief Legal Officer and the CISO care about security. If we can't get them comfortable, it doesn't matter how good our clinical outcomes are. **[SALESLOFT REP]:** That adds another stakeholder to convince. **[NANCY]:** Multiple stakeholders. This is honestly one of the things that surprised us most when we moved upmarket. In the benefits consulting channel, we were really selling to one or two people. In enterprise, we're selling to five, six, sometimes seven different stakeholders: the benefits lead, the Chief Health Officer, the HR head, Finance, Legal, sometimes CISO, sometimes the CEO's office depending on how high it escalates. Each of them has different questions. The HR person cares about engagement and culture. Finance cares about cost. Legal cares about liability. The CISO cares about security. And if any one of them says "no," the deal is dead. **[SALESLOFT REP]:** That's a complex consensus to build. How long are your sales cycles right now? **[NANCY]:** Nine to sixteen months for enterprise deals. Some have taken even longer. It's not unusual for a deal to sit in evaluation or legal review for four, five months. And during that time, people are asking us for more case studies, more security information, sometimes they want to do a pilot first before committing to a full deployment. The velocity is nothing like the mid-market space. **[SALESLOFT REP]:** Let me ask you this: who typically initiates the conversation? Is it someone who's been burned by a lifestyle app? Or is it more organic? **[NANCY]:** Usually it's one of two things. Either we're in already—like we started with an EAP or as a voluntary benefit—and someone internally sees the engagement and clinical outcomes and champions us to expand within the company. Or, it's someone who's heard about us through their peer network, maybe at a HR conference, and they reach out. It's very rarely a cold outreach that converts into a real opportunity at the enterprise level. We've tried cold calling, direct mail, LinkedIn—it's not efficient. People in the benefits space are pretty traditional. They want to know you from someone they trust. **[SALESLOFT REP]:** Speaking of peer networks and credibility, let me ask about the competitive angle. You mentioned earlier that there are 47 mental health apps on most platforms. How are you positioning against those? **[NANCY]:** This is the other existential question we're grappling with. The lifestyle apps—Calm, Headspace, Teladoc—they're cheap, they're sexy, they have huge consumer awareness. Everyone's heard of Calm. It's $15 a month. Our clinical program with licensed therapists is obviously more expensive. And they can argue they can make employees "less stressed," which is a nice benefit. But here's what they can't do: they can't treat actual mental illness. They can't help someone with clinical depression. They can't manage PTSD. They can't do anything for someone with bipolar disorder or schizophrenia. What we do is clinical treatment. We're medicine, not meditation. **[SALESLOFT REP]:** And are you able to get that distinction to land in these conversations? **[NANCY]:** It depends on who we're talking to. If we're talking to a Chief Medical Officer or a Chief Health Officer who has clinical training, they get it immediately. They understand the difference between a wellness app and a clinical treatment platform. But if we're talking to a benefits person who doesn't have a medical background, or to Finance, they sometimes see it as "well, this is more expensive, and we already have the meditation app, why do we need both?" That's where we have to educate. **[SALESLOFT REP]:** What does that education look like? **[NANCY]:** We pull data. We show them: "At companies your size, typically 8-12% of the workforce has a diagnosed mental health condition at any given time. Depression, anxiety, PTSD, bipolar, substance abuse. Of those, maybe 30-40% get treatment. And of those who get treatment, most go through their primary care doctor or the EAP, which is often a short-term support model." We then show them what clinical outcomes look like. Remission rates, recovery times, quality of life improvements. And we ask them: "Wouldn't you rather your employees with actual mental illness get proper clinical treatment instead of hoping a meditation app helps?" But honestly, Marcus, we're not always winning that argument. Some benefits leaders still choose the cheap option. Their logic is, "If it makes 70% of our workforce feel a little less stressed, that's better than an expensive program that 2% of our workforce actually uses." And I get the logic, even though I think it's short-sighted. **[SALESLOFT REP]:** That gets to the buyer education question. It sounds like you're trying to educate people on why clinical matters, but some buyers just aren't there yet. **[NANCY]:** Exactly. And that's partly a market maturity issue. The whole category of digital mental health therapy is only about ten years old. We're still in that phase where enterprises are figuring out whether this is real, whether it works, whether they should care about it. Some of the smartest Fortune 500 companies—ones with really mature health and wellness programs—they totally get it. They've moved on from "should we try this?" to "how do we measure clinical outcomes and ROI?" But a lot of enterprises are still in the "Isn't the EAP enough?" phase. **[SALESLOFT REP]:** When you look at your sales team right now, what's the biggest capability gap? **[NANCY]:** Sales acumen in enterprise health benefits. Most of my team came up through the benefits consulting channel, or they came from other health plans or insurance companies. They know how to navigate that world. But they don't necessarily know how to sell to a Chief Health Officer at a 20,000-person company. They don't know how to navigate multi-stakeholder consensus. They don't know how to write an RFP response that Finance will care about. They don't know how to position against Teladoc or manage a competitive deal. And honestly, they're scared of the CISO and the Legal team. They're used to benefits people who are collaborative partners. They're not used to an adversarial security review. **[SALESLOFT REP]:** Have you brought in enterprise sales expertise? **[NANCY]:** I'm trying. I've been recruiting people from the health insurance companies, from benefits consulting firms, people who have actually sold into enterprise benefits departments. But there's a shortage of that talent. It's a pretty specialized space. And even when I hire someone who's got the experience, they have to learn our product, our clinical story, the competitive landscape. It takes six months before they're really productive. **[SALESLOFT REP]:** What would help them be productive faster? **[NANCY]:** Honestly? Better sales playbooks. Right now, we have some playbooks, but they're not comprehensive. We have one for "selling to a benefits leader," but what about selling to Finance? What about CISO conversations? What about handling the "we're happy with our EAP" objection? What about the competitive conversation when they're comparing us to Teladoc? We need more battle cards. We need better case studies—segmented by company size, by industry, by specific use cases. We need a better discovery process that helps us identify which stakeholders we need to get comfortable with early. We need better messaging around ROI and intermediate metrics. **[SALESLOFT REP]:** And all of that requires some validation. You can't just make it up. **[NANCY]:** Right. We need to look at our customer wins. What deals actually won? Which stakeholders said yes versus no? What was the time to close? How many stakeholders did we have to convince? What was the champion's title? What was the trigger event? Why did they choose us versus the competitor? We need to be methodical about this instead of just hoping. **[SALESLOFT REP]:** That's where having a tool that helps you capture and analyze that data becomes really important. You could look at your last ten wins, understand the pattern, and then build a playbook around it. **[NANCY]:** Absolutely. And right now we don't have a great way to do that. We have Salesforce, but honestly, the data in Salesforce is messy. My reps aren't disciplined about updating it. We have call notes that are scattered everywhere. We have deal reviews, but they're not systematized. We probably have the data we need, but we're not extracting the insights from it. **[SALESLOFT REP]:** Can I ask about your deal review process? **[NANCY]:** [laughs] We have one, but it's not great. I do weekly one-on-ones with my direct reports, and we talk through their open deals. I ask them about stage, about stakeholders, about what's next. But it's all conversational. There's no structure. I don't have visibility into why a deal is stalled. I don't know if it's a technical issue, a security issue, a budget issue, or just that no one's following up. And honestly, with the complexity of these deals—six stakeholders, long sales cycles, multiple evaluation rounds—deals slip all the time. **[SALESLOFT REP]:** Walk me through what a typical deal looks like from start to finish. Let's say you've got a new enterprise prospect. **[NANCY]:** Okay, so usually it starts with an inbound inquiry or a warm introduction. Let's say the Chief Health Officer at a 10,000-person company saw our case study or heard about us at a conference. They reach out and say, "We're interested in learning more." Now, my sales rep's first call is usually discovery—understanding their current state, their pain points, their decision-making process. That call is messy because half the time the Chief Health Officer says, "Yeah, I'm excited, but I need to loop in the benefits leader and Finance." Now we're scheduling a group meeting. Before that, I'm hoping my rep has done research. Do we know who the benefits leader is? Do we know anything about their current benefits offering? Are they with a benefits consultant? All of that matters for how you position. The group meeting happens—usually it's the Chief Health Officer, the benefits leader, maybe an HR person. My rep does a demo. People ask questions. Usually someone in that meeting says, "This looks interesting, we need to bring in legal and security to review." Now you're entering the formal evaluation phase. Our team has to provide security documentation, sometimes a full security questionnaire, sometimes they want a third-party assessment. Legal wants to review our terms, our data handling, our liability. This phase can take anywhere from six weeks to six months. During this time, we might get asked to do a limited pilot or a deeper evaluation. While legal and security are reviewing, there's a parallel track with Finance. They want to see pricing, they want to model the cost, they want to know what the annual commitment is. Sometimes we're negotiating volume discounts at this point. Sometimes they're comparing us to other solutions. If we get through legal, security, and Finance without a deal-breaker objection, we usually move to an implementation and pricing discussion. Sometimes there's a formal RFP process. Sometimes it's more of a handshake. And then comes the actual purchasing, which might involve procurement, which brings yet another stakeholder into the picture. **[SALESLOFT REP]:** That is a lot of handoffs. **[NANCY]:** It's exhausting. And each one is a chance for the deal to die. Someone in legal might flag something. Security might have a compliance concern. Finance might decide the budget isn't there. Or, honestly, the whole thing might deprioritize because there's an organizational change or a different initiative takes precedence. **[SALESLOFT REP]:** How long did you say that whole process takes? **[NANCY]:** Nine to sixteen months. In some cases longer. We have one deal right now that's been in legal review for eight months. **[SALESLOFT REP]:** And what's the conversion rate on opportunities that get into the formal evaluation phase? **[NANCY]:** [pauses] Honestly, I wish I had that number cleanly. My gut tells me it's maybe 40-50%. We lose deals to budget, to competitive offerings, to security concerns that never get fully resolved, to organizational changes, or sometimes people just decide to wait and see if the market matures. **[SALESLOFT REP]:** What would help you close more of those? **[NANCY]:** Having a clear playbook for different objection scenarios. Right now, if a deal is in legal review and legal has a concern, my rep kind of has to figure it out. They're calling our legal team, asking questions, sometimes getting inconsistent answers. We need a structured way to handle security and legal objections. We need to know what our standard negotiation points are. We need to empower reps to move deals forward instead of having everything get stuck in internal back-and-forth. And we need to be proactive about the budget conversation earlier. The problem is we usually don't find out there's a budget issue until we're deep in the process. By then, we've spent a lot of time and energy. If we could figure out in the discovery call whether there's actually budget, whether they're going to have to get board approval or Finance approval, that would help us prioritize our effort. **[SALESLOFT REP]:** Right. You'd rather know early whether a deal is real. **[NANCY]:** Exactly. And honestly, I think a lot of our deals die not because of product-market fit issues, but because of process issues. We're not asking the right discovery questions. We're not managing stakeholders proactively. We're surprised by objections that should have been anticipated. And we're not following up consistently. **[SALESLOFT REP]:** Let me ask you about something broader. You mentioned you're at $35M ARR. Where do you want to be in three years? **[NANCY]:** $100M-plus. At least. The market is there. Enterprise benefits spend on mental health is going to grow. But we have to figure out how to scale the sales organization in a way that makes sense. We can't just hire a bunch of sales reps and hope they figure it out. We need a motion. A playbook. A way to systematize this. Right now, we're still pretty dependent on my ability to jump into deals and move them forward. We have maybe two other people on my team who can do that, and we need to build that capability across the entire team. **[SALESLOFT REP]:** And that requires having data about what works. **[NANCY]:** It does. We need to understand: what are the characteristics of a deal we're likely to win? What's the right sales cycle? Who are the champions? What's the decision-making process? What are the objections, and how do we overcome them? What's the right sales methodology? Right now we're kind of making this up as we go. **[SALESLOFT REP]:** I think that's where Salesloft and Clari could be really valuable for you. One, we help you capture the data from your deals—the calls, the emails, the notes. Two, we use AI to analyze that data and extract insights about what's working. And three, we help you apply those insights into plays, coaching, forecasting. So instead of flying blind, you have a data-driven understanding of your sales motion. **[NANCY]:** That sounds useful, honestly. The question is: how quickly could we implement and start seeing value? We're hiring people now. I need to be able to ramp them faster than six months. **[SALESLOFT REP]:** Fair question. If you're willing to invest time in getting the data set up—like making sure Salesforce is clean, making sure your teams are recording and transcribing calls—we can probably generate some useful insights within 30-60 days. You'd start to see patterns, playbooks, objection handling, and you can start coaching people on those. **[NANCY]:** And I assume there's a cost to this? **[SALESLOFT REP]:** There is. We have enterprise plans that typically run $50K-$100K a year depending on team size and usage. For a team your size ramping to 20-30 reps, you'd probably be in that range. But the ROI, if you can shave even a month or two off your sales cycle, or improve your win rate by 10-15%, that pays for itself pretty quickly. **[NANCY]:** I appreciate that framing. Let me think about it. We have a lot of tools already—Salesforce, a dialer, some analytics. What would make me want to add another tool? **[SALESLOFT REP]:** Great question. Most of the tools you have are point solutions. They're good at what they do. Salesforce is great for CRM, your dialer is good at making calls. But none of them are designed to help you understand your sales process and scale it. They're not asking the question: "What do our best sales reps do differently?" None of them are helping you coach your team in real time based on actual call data. And none of them are helping you forecast accurately. Clari, in particular, is really good at taking messy forecast data and actually predicting what you're going to close. **[NANCY]:** We have huge forecast accuracy problems. People are always over-optimistic about their deals. Deals they say are 80% confidence close, and then they slip. **[SALESLOFT REP]:** That's pretty common. And the reason is that reps don't have visibility into what's actually happening in their deals. They have a gut feeling, but they don't have data. Clari looks at all your communications—calls, emails, meeting notes—and gives you a probability score for each deal. So instead of "I think this is an 80% close," it's "Based on the activity we're seeing and the stakeholders involved, this deal has a 42% probability of closing." **[NANCY]:** That would be a game-changer for forecasting. My CFO asks me every month what we're going to close, and I usually answer with a pretty wide range because I just don't know. **[SALESLOFT REP]:** That range probably costs you. Your CFO probably doesn't trust your forecast, so she builds in a buffer or doesn't plan headcount around your numbers. And you look bad when you miss. **[NANCY]:** Absolutely. And then the next month my credibility is damaged, and it's harder to fight for headcount or resources for the sales org. So yeah, I'd love to have better visibility. **[SALESLOFT REP]:** Here's what I'd suggest: Let's set up a working session with your team. We'd look at five or six of your current deals—a mix of different sizes and stages—and we'd do a deep dive on what's really happening in each one. We'd look at call recordings, emails, notes, and we'd extract the real status versus what's in your forecast. I bet we'd find a gap. **[NANCY]:** I'm sure there's a gap. I'm game. But I want to make sure this is actually going to help us in the next 30-60 days. I need quick wins. I need to show my team that there's a better way to sell this product. **[SALESLOFT REP]:** Totally reasonable. And here's the honest truth: the quick win is probably in getting your existing deals unblocked and moving. You probably have $5-10M in pipeline right now that's stuck somewhere. If we can identify why it's stuck and help you unstick it, that's an immediate impact. That's easier than waiting for new playbooks to create new demand. **[NANCY]:** We definitely have deals that are stuck. That's actually a huge frustration. I feel like we're always firefighting—jumping into deals that are about to die instead of proactively preventing them from stalling in the first place. **[SALESLOFT REP]:** Right. And I think with better visibility and process, you'd shift to more prevention and less firefighting. But that does require investment in the tool, in data quality, and in rep adoption. **[NANCY]:** My team can be resistant to new tools. We've implemented a few things that didn't stick. So I need to make sure this is something they actually want to use, not just something I'm forcing on them. **[SALESLOFT REP]:** Fair. What would make them want to use it? **[NANCY]:** If it actually helps them close deals. If they see that the insights are real. If it makes their life easier instead of creating more work. Right now, they're busy prospecting, doing discovery, handling objections. If a tool just creates more data entry and reporting, they'll resent it. **[SALESLOFT REP]:** We actually talk about this a lot. The tools that stick are the ones that solve a real problem for the rep, not just for management. For a rep, the real problem is, "I have a deal that's stuck and I don't know what to do." Or "I'm supposed to close this deal, but I'm missing information." If our tool helps them unstick a deal or gives them the information they need, they'll use it. **[NANCY]:** Okay, I hear you. Let's do it. Set up that working session. But I want to make sure we're also having a conversation with my team. I want them to see the value too, not just hear it from me. **[SALESLOFT REP]:** I think that's smart. How about this: we set up a 90-minute workshop with you and 3-4 of your top reps. We walk through the process, we analyze a few deals together, and we show the team what we can do. If they're excited, we move forward with a pilot. **[NANCY]:** That works. And look, I appreciate the conversation. This has been helpful. Honestly, just hearing you articulate the problem—the deal stalls, the forecast gaps, the process inconsistency—that validates what I've been feeling. I know we have issues. I just haven't had a framework for thinking about them. So even if we don't end up using Salesloft, this conversation has been useful for clarifying what needs to change. **[SALESLOFT REP]:** That means a lot. And I think you're at an interesting moment. You've got a product that works, you've got demand, you've got a market opportunity. The constraint right now is the sales motion. You're trying to build a scalable, predictable enterprise sales process, and you don't have that yet. That's actually the biggest value of tools like ours—not in the features, but in the discipline and visibility they force you to have. You have to think hard about your playbooks. You have to be honest about your forecast. You have to coach your team. And once you have that, you can scale. **[NANCY]:** I appreciate that. You're right. We're at a pivot point. We can either figure this out and scale efficiently, or we can hire more people and hope they figure it out, and that's going to be slow and expensive. So yeah, let's explore this. Send me the details on the workshop. I'll get my team aligned. **[SALESLOFT REP]:** Will do. And Nancy, one more thing. When we do that workshop, I want to make sure we also talk about your long-term motion. Like, is the goal to hire 20 more reps in the next year? Are you going to have regional teams? Are you going to build a partner channel? Because that affects how we think about the tool and the process. We want to build something that scales with you. **[NANCY]:** That's a great question. Honestly, I think we're going to do some of everything. We'll probably hire 10-15 reps internally to focus on direct enterprise sales. We're exploring partnerships with the big benefits consulting firms—they already have relationships and they can sell our solution alongside their services. And we're thinking about international expansion, probably next year. So yeah, we're going to grow fast. **[SALESLOFT REP]:** That's ambitious. And it's also why having a solid foundation now is so important. You're going to have distributed teams, you're going to have different sales models, and the only way to keep consistency is to have a clear playbook and good visibility. **[NANCY]:** Understood. Let's do this. **[SALESLOFT REP]:** Awesome. I'll send over the workshop proposal today. And Nancy, thanks again. I know you're slammed. This was really valuable. **[NANCY]:** Thank you, Marcus. I appreciate you taking the time to understand our business before jumping into the pitch. --- ## Summary of Key Takeaways ### Business Context - **Company Stage:** $35M ARR, transitioning from mid-market/channel motion to direct enterprise sales - **Market Challenge:** Scaling sales team from benefits consulting expertise to enterprise-grade selling - **Team:** ~8-person sales team with strong mid-market skills but limited enterprise experience ### Critical Pain Points **1. Budget Constraints & ROI Gap** - Mental health benefits budgets are flat or declining across enterprise accounts - Nancy's team must justify reallocation from existing EAP/insurance spend, not growth - Finance approval requires 3-5 year ROI model, but benefits leaders have 12-18 month tenure horizon - Intermediate metrics (clinical improvement) don't satisfy Finance requirements for ROI - Lack of Fortune 500 case studies creates credibility gap for outcomes claims **2. Stakeholder Complexity & Sales Cycle Length** - Enterprise deals require consensus from 6-7 stakeholders: HR, Benefits, Finance, Legal, CISO, sometimes CEO - Sales cycles: 9-16 months (some up to 20 months in legal review) - Current deal conversion: ~40-50% from formal evaluation phase - Multiple stakeholders create multiple points of failure - Current deal review process is informal; Nancy lacks systematic visibility into stalled deals **3. Privacy & Security Concerns (Rising)** - Post-competitive security breaches, enterprises now require third-party assessments - CISO and Legal teams demand detailed security documentation - Must earn trust separately from clinical value proposition - Mental health data sensitivity higher than other health information **4. Competitive Positioning vs. Lifestyle Apps** - Market still in education phase: buyers conflate clinical therapy with wellness meditation - Low-cost alternatives (Calm, Headspace, Teladoc) have high consumer awareness - Benefits leaders sometimes choose cost over clinical efficacy - Nancy's team struggles to articulate clinical value vs. wellness benefits - Buyer education is required but time-consuming **5. Immature Enterprise Sales Motion** - Insufficient playbooks for enterprise scenarios (Security/Legal objections, Finance positioning, competitive handling) - Team lacks battle cards and segmented case studies - No systematic process for identifying champions or decision-making structure early - Sales reps dependent on Nancy's direct involvement to move complex deals - Forecast accuracy problems (reps over-optimistic; no data-driven probability scoring) - Hiring and ramp time: 6 months to productivity ### Strategic Opportunities - Unblocking $5-10M in stalled pipeline (quick win) - Building replicable playbooks for different stakeholder types - Developing competitive positioning battle cards - Systematizing discovery to identify budget/decision structure early - Improving forecast accuracy for CFO credibility - Scaling from 8 to 20-30 person team in 12 months ### Next Steps - 90-minute working session with Nancy and 3-4 top reps to analyze current deals - Deep dive on deal stalls and forecast gaps - Pilot program if team sees value