Your Guide to the Hottest New Role in Software: Sales-Assist

March 9, 2022

As recently as 2016, Slack Co-Founder & CEO Stewart Butterfield emphasized that Slack intended to keep relying on organic and viral growth rather than a large sales force. Back then he told Business Insider, “I think we can get away without having a sales team in any kind of traditional way probably forever.”

The best PLG businesses solve end user pain, distribute where those users live, make it easy to get started, deliver value before the paywall and then hire sales last.

But they do hire sales!

In Slack’s Q2 FY2020 earnings call, Butterfield described the company’s current go-to-market approach as always starting with the end user, which allows Slack to go ‘bottom-up’ and ultimately win million-dollar enterprise deals. Here’s what he said on the call:

“In every case, our sales team had the advantage of a lot of very happy end users. Our history of strong bottom-up adoption is a vital factor in our success. We only win if people choose Slack, and they choose Slack if it provides real value to them. There is no other path.” – Stewart Butterfield

It even turns out that one element of user pain is not having someone to help them fill out security questionnaires, navigate purchasing processes and work through legal requirements for things like GDPR. Contract size used to dictate when procurement got involved. Now even free tools may go through the same level of scrutiny if important data is involved. Sales can actually enhance the user’s experience by helping guide them through the buying process rather than forcing them to go it alone.

The hottest role in PLG: ‘Sales-assist’

There are very real risks in bringing sales into a self-service business.

An overly aggressive sales team could turn off prospects who just want to use the product and be left alone, cannibalizing self-service conversion. Sales could push the product roadmap towards larger customers with deeper pockets, which could lead to a more complicated and harder-to-use product. And, let’s be honest, sales is expensive and can drive up CAC significantly. In many companies, it can start to feel like you’re building two different companies at the same time.

So what should sales look like?

Enter the hottest PLG sales role: sales-assist. These sellers—also called onboarding specialists (Airtable), success coaches (HubSpot), user operations (Asana), and enterprise advocates (Atlassian)—partner with Product Qualified Leads (PQLs) to improve their product experience and navigate the buying process.

Sales-assist reps may work with users pre-conversion or post-conversion. What matters is whether they can uncover friction in the user’s buying process, remove that friction, and guide users to be more successful.

OpenView is actively working on our 2022 Product Benchmarks report to help PLG operators compare themselves against their peers across the metrics that matter most. Please consider taking our 10-15 minute survey!

Sales-assist at Zapier

Zapier, the popular automation startup valued at $5 billion, had raised only $1.3 million in funding to scale to a mind-boggling $140 million revenue run-rate as of March 2021. The company grew extremely quickly and profitably by focusing on PLG paired with self-service purchasing (I’m a big fan of their approach to product-led marketing).

Now Zapier is turning to sales-assist to help fuel its next phase of growth. I sat down with Steeve Vakeeswaran, head of sales and expansion, to learn about how Zapier tested sales and what they’ve learned along the way.

Steeve was initially hired into a “BizOps/special projects” role in early 2020 only a week before the pandemic. His role was to support a cross-functional effort to launch Zapier’s Company offering, their highest grade product aimed at customers needing enterprise-grade features and support.

Unlike many other enterprise-level products, Zapier’s company offering isn’t gated behind a “contact sales” form. The price is fully transparent, starting at a comparatively affordable $599 per month. Anyone can try and buy the company tier on a self-service basis.

Zapier’s pricing page

Steeve and his team quickly learned that upmarket customers, those buying on behalf of a company rather than a team or startup, had a different buying process and procurement process compared to other Zapier customers. Even though upmarket customers had everything they needed to self-serve, many of them just weren’t doing it. A purely self-service model wasn’t going to cut it if Zapier wanted to achieve the scale of success that they had seen with down-market customers.

Zapier contemplated adding in a sales team; however, there were many open questions about how that team should look and whether it would improve upon Zapier’s already successful self-service motion. As Steeve contemplated sales at Zapier, he followed a four-step process: (1) understand the customer journey, (2) validate that sales improves on natural growth, (3) define the right plays, and (4) be thoughtful about compensation and operations.

Step 1 – Understand the customer journey

Before jumping to a solution, Steeve wanted to gather more data and talk to customers who were experiencing friction. He became Zapier’s first sales rep, a role Steeve held for about six months. His first objective was to learn as much as possible about the upmarket customer’s buying process:

  • Why weren’t they comfortable self-serving into the product?
  • How do they go through the process of buying a product like Zapier? What approvals were required?
  • How did they need to purchase a product like Zapier? Could they use a credit card?
  • Where did customers get stuck or have questions?

He discovered things that might seem intuitive for traditionally sales-focused companies. Some folks had to go through several layers of approval and struggled to navigate that on their own. Others were hesitant to put $7,000+ on a credit card and wanted a different billing mechanism. And some just wanted to talk to someone at Zapier to make sure they would be supported through implementation and beyond.

Step 2 – Validate that sales improves on natural growth

Zapier didn’t want to add salespeople for the sake of adding sales; they wanted to demonstrate that sales actually improved on their baseline metrics relative to self-service. In the first 90 days, were folks who went through guided onboarding setting up more zaps, inviting more people on the account, activating more workflows, etc.? Were existing self-service customers who worked with an account manager more likely to expand their spend with Zapier than those who didn’t?

By being thoughtful about Zapier’s experimentation process, Steeve started to gain confidence in the benefits of a sales motion and what would happen if they replicated it. He found that sales touchpoints weren’t just helpful for converting upmarket accounts, but even improved retention rates post-purchase because Zapier was able to gather so much more information on who these customers were and what they needed.

The cherry on top: additional customer touchpoints created a powerful feedback loop that fed back into the product, allowing Zapier to improve the experience for self-service accounts as well.

Step 3 – Define the right plays

In product-led sales, the goal is to engage the right accounts at the right time with the right message based on what you know about them. That can be extremely daunting when you’re starting from scratch.


PQL maturity curve

Steeve’s team started looking closely at different signals that might qualify a customer for a sales-assisted experience. One big qualifying factor was a simple one: they actually expressed interest by requesting a demo. Zapier isn’t gated behind a demo; a demo is an opt-in decision that the customer makes.

If the customer doesn’t initially request a demo, Zapier now uses a few different metrics to qualify an account as a product qualified lead (PQL):

  • Multi-player use: Are there multiple active users on a specific domain using Zapier?
  • Usage patterns: Is the account growing its usage over time? Are they seeing seasonal variability in usage?
  • Use case: Does the customer’s use case for Zapier—defined based on the depth and variety of apps they’re using – indicate that they’d benefit from assistance?
  • Role: Does the user’s role align with Zapier’s ideal customer profile and where Zapier sees the most success (ex: marketing and marketing operations)?

Zapier’s sales-assist reps then tailor their outreach based on user’s context in order to add as much value as possible. For example, if an account has multiple users on a domain, the rep might suggest consolidating those users into a corporate account, which allows folks to collaborate and lets them benefit from a pooled usage allotment.

Step 4 – Be thoughtful about compensation and operations

Steeve paid special attention to hiring the right types of individuals. He wasn’t just looking for past SaaS sales experience; he was looking for experience with the Zapier product. It was important for candidates to be comfortable using Zapier, able to brainstorm with different customers and be genuinely curious individuals.

Snapshot of Zapier’s Sales-Assist Representative job description

In the initial stages of testing sales-assist, Steeve made the decision to compensate everyone on a 100% base structure. That way team members wouldn’t have to worry about variable commissions and could instead prioritize setting a strong foundation. He wanted to encourage feedback loops with product, marketing, billing, and legal as well as documenting winning motions that made sense for the team. Individuals are rewarded based on team success, measured on a quarterly basis, rather than their own quota retirement.

One counterintuitive winning motion at Zapier came from creating a feedback loop between customer support (called customer champions) and sales-assist. With support being on the frontlines interacting with thousands of users, Zapier looked for ways to pass relevant accounts from support to sales-assist. That needed to happen in a natural way; Zapier didn’t want users to feel artificially pressured or upsold. The company now generates a steady stream of support qualified leads eager to talk to sales.

This process has clearly paid off for Zapier. They’ve already scaled the sales-assist team from one to 10 people, and it’s one of the fastest-growing teams within the company. The future of sales-assist at Zapier is bright.

Want to learn more? Learn how you leverage the sales-assist by joining Kyle Poyar’s Growth Unhinged.

Kyle Poyar

Partner at OpenView

Kyle helps OpenView’s portfolio companies accelerate top-line growth through segmentation, value proposition, packaging & pricing, customer insights, channel partner programs, new market entry and go-to-market strategy.