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Hypergrowth Go-to-Market: Toss Out the Playbooks and Start Experimenting Sooner


    Billy Sheng is the VP of Inside Sales at Esper, a DevOps platform for managing dedicated devices at enterprise scale. Esper’s first sales leadership hire, Billy has been a central figure in that company’s explosive growth. Below he shares how Esper catalyzed top-tier growth by pursuing multiple GTM motions simultaneously.

    Product-Led Growth is rightly the go-to sales motion for startups tackling large addressable markets where your product can effectively do the early selling. As the first sales leadership hire at Esper, where we tackled category creation around “DevOps for Devices”, we decided to develop multiple sales motions far earlier than conventional wisdom says you should.

    Our belief was that PLG alone wasn’t going to be enough to fuel top-tier growth from $0 ARR onwards. In a world where 5x is the new growth rate standard from $1M in ARR, I think of our approach as “PLG Plus” where we leaned on dev-focused self-serve while also simultaneously experimenting with many other sales motions.

    Infrastructure software for hardware (dedicated device fleets) can be a slow moving sale, so a lot of our work focused on how to accelerate the customer journey knowing that things like testing and buying decisions simply take longer.

    This blog is a recap of what worked for us.

    The Standard Playbook Is Evolving with the Times 

    It’s a credit to HubSpot that their GTM strategy remains the standard playbook for traditional SaaS business models. Start with an inbound motion fueled by content to fill the funnel, then sell them something. Optimize percentages. At around $10M in ARR, add another motion like enterprise outbound.

    For many companies that pursued this approach, the model worked well because teams perfected a single motion before moving onto another. Early personnel decisions were also easier. You just needed to land on a sales formula and hire people who could execute. Your investors were overjoyed if you could triple sales each of your first years (T3D2).

    The ratcheting up of growth expectations to that 5x level resets the playing field. Companies need to jump into experimentation earlier, especially on their enterprise sales motion or partner channels. It can be harder to hire your first sales lead because you’re going to need them to be effective with two or three or four sales motions.

    PLG Plus Helped Esper Achieve 5x Early-Stage Growth 

    The decisions we made at Esper came from the fact that we’re creating a new category around DevOps infrastructure for enterprise devices (think of kiosks in retail locations or order tablets in restaurants). This was actually an advantage because from the beginning the founding team was open to creative thinking and new ideas. What started as sometimes painful trial and error turned into a flexible new GTM approach.

    Here’s what we learned.

    Smart experimentation. If PLG alone won’t drive enough activity, you need to take other actions to generate a healthy ecosystem in the funnel. Start with a clear understanding across the entire leadership team on:

    • How many sales motions you’re going to attempt
    • Which ones

    Start by looking at the collective experience of your founder(s) and your sales lead(s). Those motions are going to be the natural place to start. In Esper’s case, our CEO knew first-hand how engineers test infrastructure products from his time at Amazon and Microsoft while our COO had Biz Dev, OEM, and Partner channel experience. I added the traditional inbound and outbound skill set.

    The key point is to leverage your founding team’s existing expertise. Let that determine how many experiments to try in the early going.

    I emphasize “experiment” because not all of them are going to work. Timing is everything. For instance, we halted the BizDev motion early then returned to it later when we found the right executive to own that motion. If you find you’re not gaining traction in an area, don’t hesitate to move on.

    Finding the right sales lead. The traditional sales talent playbook says that hiring a VP of Sales who leans enterprise can slow down early growth. Esper’s playbook of early GTM experimentation meant that a startup veteran VP of Sales might not have seen some of the later stage sales motions first hand, and thus might struggle later.

    What worked for us was leveraging the founding team’s expertise to fill in the gaps. Remember to make sure that you have your founder’s commitment to dedicate the time to sales. They’re playing more of a role here than they need to using the standard inbound playbook.

    Know when to cut bait. Understanding why something isn’t working can be hard too. Not every sales motion we tried gained traction right away. It’s critical to know when something isn’t going to work with your current team and/or product maturity.

    Here is my mental model for making decisions on whether to commit to a particular motion:

    • Try a new sales motion.
    • If it doesn’t attract someone who feels strongly and wants ownership, move on.

    If someone on the team doesn’t feel that they can make a living with it, cut it.

    But not (necessarily) forever. Revisit those “failed” experiments as your team evolves. Esper hired a really experienced enterprise sales exec later who came in and resurrected one of our halted channel efforts. That changed the calculus entirely.

    Marketing’s more complex role. One implication of early GTM experimentation is that Marking has a lot more sales motions to support. We had two big ah-ha moments:

    • Hire Marketing early. Just as your Sales team looks different in this model, so too will your Marketing team. Bring great people early because they are going to have a lot of work to do getting up to speed. To take just one example, you’re going to need custom content to complement each sales motion.
    • Staffing levels will be different. Esper chose to structure teams within Marketing focused on a particular sales channel. Our Marketing team headcount was almost 1:1 with Sales. The inbound playbook would see Sales at 2x or 3x the Marketing team.

    We were careful not to hire until we had a good sense a particular sales motion was taking off. By front loading our investment in Marketing, we were much more nimble early on. This was another important factor in Esper achieving 4x hypergrowth right out of the gate.

    Every company faces a unique set of challenges when it comes to GTM strategy. I hope hearing a little about what worked for Esper – solving the challenges of category creation in a high growth world – will help accelerate your own GTM out of the gate.

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