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Strategic Communications Advisory For Visionary Founders
11 HR Tech Founders
Enterprise Sales Lessons
Map the Real Decision Authority Before Designing Your Sales Motion
When Metaview ran top-down sales processes, they kept running into a dynamic where the formal buyer wasn’t actually making the call. Siadhal found that “the aggregate weight of authority of the end users is actually higher potentially than the senior leader in this function.” The reason was structural. “The end users are, yes, they’re recruiters who, they matter a ton, but it’s also every hiring manager,” and as he pointed out, “some of these hiring managers are VP’s of engineering, VP’s of sales, whatever it might be. Some of these hiring managers are CEO’s.” His conclusion was direct: “the aggregate weight of that voice is a lot larger than the buyer.”
Land Enterprise Accounts Through One Leader With a Felt Pain
Jennifer Dulski built her enterprise motion around a simple wedge: find the functional leader who is already feeling the pain and has budget to act. Rather than selling top-down through procurement, her team targeted “functional and divisional leaders at large companies who have these pain points. So sometimes it’ll be a CMO or a CIO or a VP of engineering who says, “I really want something like this for me, you know, they’re feeling disconnected.” From there, the motion was designed to let results do the selling internally. As Jennifer described it, “we enter a company in that way, and then the data shows how well it works. And then other people inside the company want to get involved and use it for their organization.” The account expands not because of a sales push, but because proof travels through the org on its own.
Qualify Every Enterprise Deal Against the Buyer's Top Two Priorities
Nitzan shared how Benivo qualified enterprise opportunities: if the problem being solved was not near the top of the decision-maker’s list, the deal was not going to close. “It has to be on their KPIs and their OKRs. If the problem I’m trying to solve is not on the person’s number one or two list of priorities, it’s never going to work. It’s going to be very tough to do a sale.” This shaped how deeply Nitzan invested in understanding each buyer before pushing for anything. The relationship-building was not just rapport for its own sake, it was intelligence-gathering. “For that person I can tell you the name of their children and I can tell you what their kids like to eat and like to do. It’s that level of relationship to get to know and of course to know their objectives.” Knowing the person and knowing their priorities were the same job.
Use Platform Partner Sales Teams to Navigate Enterprise Accounts
Selling into large enterprises is expensive when you’re flying blind, and Hanns found a way to fix that by embedding Cobrainer’s motion inside the sales organizations of major HR platform vendors. “Working with these big HR players and actually working with their sales organization, pushing us, pushing our solution really helped us a lot. So that kind of just scaled, that just made us very efficient as a sales organization because we were able to talk to the sales force of say, SAP and they helped us in navigating who to talk to with these large enterprise players.” The partners didn’t just open doors, they also helped cut losing deals early. “They also kind of helped us by saying, hey guys, we heard you’re talking to this and this company, just stop talking to them. They have other priorities right now. Don’t focus on them, focus on other companies.” The net effect was a much tighter pipeline: “this helped us segregate which kind of opportunities to double down on and which ones who were kind of seemingly going in the right direction, but were probably then taking longer than expected.”
Lead Enterprise Deals With the Use Case That Pays Back Fastest
Michael’s approach to enterprise sales was built around a simple prioritization filter: start with the use case that generates measurable value fastest, then expand from there. “For us it really starts with use cases that we know will drive revenue pretty immediately,” he said. In practice, that meant targeting companies with large field sales forces where upskilling was a pressing operational problem. “There’s a subset of companies where they have a large field sales force and upskilling that sales force is absolutely mission critical and very difficult as well, and so from our point of view, that’s sort of where we provide value more immediately.” Rather than leading with a broad platform pitch that required a long proof horizon, he used the sales team use case as the entry point into the account. “We find that working directly with sales teams for product training is the best first step. And there’s a ton of use cases that flow down from there.”
Stop Sending Cold Outbound to Enterprise Buyers
Charlotte watched cold outreach collapse as a viable enterprise channel and made the call to stop entirely. The infrastructure working against her was no longer just buyer indifference. “Especially in the past two years for enterprise sales in particular, a lot of those doors have shut. Like there are spam filters on every enterprise account. If you’re attaching HubSpot tracking and stuff, it’ll just automatically decline.” The volume problem made it worse: “We’re just all inundated with emails all the time from randoms and strangers that like you don’t read them anymore and I don’t read them anymore.” After pushing through it hoping for a turnaround, the data made the decision for her. “At the beginning of this year we were like, this isn’t working. We’re not getting any type of conversion. We’re spinning our wheels. We’ve set up this whole cold calling and all this different stuff and none of it’s really yielding anything.”
Celebrate Only When Your Enterprise Buyer Starts Celebrating
Barb built a specific cultural rule into her sales team around what she called “enterprise empathy,” and it started with reframing the close. “You’ve got to have a lot of empathy when you’re selling AI into an enterprise, and a lot of empathy, particularly if you’re selling it into HR. This concept of enterprise empathy, and to respect the fact that if you’re going to celebrate when your team signed the deal, your client is freaking out at that point because they’ve just made this massive investment and it’s a risk.” The signed contract is not the finish line for the buyer; it is the moment their exposure begins. So Barb set a clear internal standard: “One of the things that I try with our sales team is we should only celebrate when they’re celebrating, to create this culture of empathy and to recognize what’s at stake for them when they sign on to that transformation.”
Expand Your Coverage to Match What Enterprise Buyers Actually Need
When Andela started moving upmarket, Jeremy quickly learned that larger enterprise customers had requirements that smaller customers didn’t. The constraint wasn’t product quality or pricing. It was geography. As he explained, “as we moved up market, it became clear we need to be able to say yes more frequently to larger companies that we worked with, which meant we need to be able to cover more time zones around the world.” The goal became building “the utility, this global talent cloud, to make it easy for the best person or the best team to work with the right company” in a way that “just didn’t exist, but needed to.” For operators moving upmarket, the ability to close larger deals often depends on whether your product can meet enterprise buyers where they operate.
Budget for Longer Sales Cycles Before Moving Upmarket
Moving upmarket changes almost everything about how you sell, and sales cycle length is the first thing that breaks if you aren’t ready for it. At Crosschq, Mike Fitzsimmons watched cycles stretch dramatically as the company pursued larger deals: “Sales cycles are longer, right. Sales cycles are six months now instead of one month. As you’re moving up market and moving those larger opportunities.” The scrappy founder-led motion that closed deals in weeks gave way to something that required more structure: “now we look like a more traditional enterprise sales team.” At the same time, Mike noted that “digital marketing wholly has become incredibly challenging. CAC is going through the roof,” with the team putting “more efforts into hand to hand combat, more efforts into live events and things of that nature.”
Build Your Buyer Map Before You Pitch Enterprise Accounts
When Electives moved upmarket, Jason’s assumed buyer map turned out to be wrong in ways that mattered. “I think we naively assumed that there’s the HR team, there’s the learning and development team, and there’s the DEI team, and those are the main folks.” The reality inside larger organizations was far more distributed. “There’s leaders of employee resource groups who are looking to bring learning to their team. There’s the head of the sales team trying to upskill their sales team, and you go down into all of the different teams and departments and there’s someone trying to upskill or develop folks on their team somewhere.” Mapping that full buyer landscape changed how Jason thought about selling into and expanding within enterprise accounts.
Sell Directly to the Leader Accountable for Team Performance
Prem Kumar built Humanly’s sales motion around reaching the person accountable for team output. “This is generally a top down sales,” he said, describing a deliberate choice to pursue decision-makers over individual end users. The target was specific: “selling to like a head of talent or director of talent so they can make their team more efficient versus an individual person picking it up.” This framing shaped who the sales team called and how they framed the value of the product in conversations. When the buyer owns the team’s results, the conversation centers on efficiency and organizational impact rather than individual features.