It's time to send in the cavalry

Part 3/3 of the Expansion Manifesto

Rahul Krishnan and Ruchin Kulkarni

Jan 24

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For Zapier, it was around the $140M ARR mark. Dropbox - at around $100M. Slack? $50M. Github - $25M.

Word of mouth, viral loops and referral mechanisms can get you far and wide and deep within accounts, but there comes a time in every PLG company’s life when it’s time to send in the cavalry. Sales.

Avengers Assemble Ready GIF - Avengers Assemble Ready ... — Your average PLG company the second it hits $25-$50M in ARR

For enterprise-wide adoption, your product has to reach new users (even those who aren’t natural adopters), new teams where it solves new use-cases, then enable new features that may not be compelling to individual users, but are to the collective - improved security, support, SSO - and all the other squiggly lines on the bottom right corners of pricing pages.

“It’s worth all the money. Personal and team accounts were steady eddy, but enterprise growth was 100% a year.” - Paul St. John, former VP of Worldwide Sales at GitHub

That you’ve hit PMF and have hit the double/triple digit ARR through a pure self-serve model are perhaps good indicators that it’s time. But a more subtle tell, and where top-down sales becomes a true force multiplier is when the organic expansion levers are working and you have penetration within accounts.

Source: a16z research (pre-2022). Zapier introduced a sales motion at $140M in 2022.

“…what we’re doing [at Figma] is taking a lot of this bottoms-up energy and excitement and turning it into this enterprise-wide sales adoption. That’s what we’re seeing being really successful.” - Kyle Parrish, Figma’s VP of Sales

Docking the bottom-up flywheel to a top-down sales engine is a maturing science. One calls for the guile and craft of a Rembrandt brushstroke. And the other is like passing a bill in congress. Making the two work in tandem is a feat that very few have managed to do well.

Part 3 of the Expansion Manifesto is on just that: On how the best PLG companies use top-down sales as a force multiplier on top of a self-serve motion to drive expansions.

Toplyne analyzes product-usage data to surface expansion and conversion opportunities in your CRM. Here’s how it works, in 1 minute:

Take it for a spin 🤸🏻‍♀️

Breaching the product/human interface 〰️

Crossing the product-human barrier brings into play, along with traditional sales, a powerful weapon in the conversion arsenal of PLG companies: a sales assist. Called “success coaches” at Hubspot, “user operations” at Asana, and “Onboarding specialists” at Airtable, sales-assist steps in to guide users into defined paths of expansion through product-education, feature adoption, etc.

The million-dollar question for sales-assist is this:

At what point of the user’s journey within the product do they step in, if they should, at all?

*wears monocles, clears throat* As a self-serve purist, I refuse to talk to your sales team, good sir.

Well, that depends on the user. The “not yets” just aren’t ready and the “self-serve purists” do not want to talk to humans. Forcing a human touch for these two cohorts of users can be damaging to user experience, and turn users away completely, leading to churn.

Hand-raisers 🙋🏻‍♀️

Hand-raisers will stand up, raise their hand and tell you that they want to talk to someone from your team, breaching the product/human interface voluntarily.

“We started from hand-raiser PQLs, where customers submit a sales contact form directly inside the product, and saw a 3x higher conversion rate than with typical MQLs.” - Hila Qu (former Director of Growth), on Gitlab’s handraiser motion

Fence-sitters 🧐

Your Product-Qualified Leads are finding value from your product already, and are primed for expansion/conversion. It’s time to extend a hand. Nudges or notifications powered through tools like Appcues and Braze actively encourage or incentivize a hand-raise within the product.

Friends don’t let friends send mass nudges to all their users.

These nudges are most effective when they’re cognizant of who, where, and when - the user, the placement, and the timing.

The who - In an ideal world, you’re triggering only the decision maker/product administrator, while keeping the product experience “pure” for all the others on the team.

The where - Configuration management screens, installation pages, admin panels are primed for expansion pathways.

The when - When are your users doing something on your product other than using it for the day-to-day? Like configuring new features, for example.

Passing a bill in enterprise congress 🧾

At this point, the product/human interface has been breached, ‘sales-assist’ has stepped in to upsell users to team/pro plans and likely looped in post-sales roles at the same time: account management and customer success.

“When paired with the right penetration heuristic, the bottom up motion serves as an important pipeline generator for the most successful top down sales.” - this a16z blog post.

As far as your top-down sales teams are concerned, it’s go time. But an enterprise-wide deal is akin to getting a bill passed in congress. The lead-cycles are long, incumbents are aplenty, and there are many stakeholders involved - so many: legal, security, compliance, the senate, the Galactic republic.

Prioritize: Feed your sales teams the hottest accounts based on product-qualification and expansion inventory (what’s the headroom for expansion in target accounts? Prioritize accounts with high headroom rather than 1st deal size.)

Find your champion: Let the product-usage data be your guide. Analyze account-level user signals to find a champion who will rally your cause from within.

Have eyes and ears within: Post-sales roles are your eyes and ears within accounts to stay alert for prime expansion moments (M&As, stack upgrades, new product launches, etc.)

Avoid deal creep: Front-loading too many features, products, or solutions and involving other teams who may also be interested in your product can confuse your core initial set of users and sabotage the larger opportunity.

Embed deeply in existing workflows: Sales assist, account management, and customer success teams parallelly invoke network and cross-network effects to ensure your tool’s deeply embedded into existing workflows.

At Figma, where cross-network effects completely transform product-development at user accounts, account management teams own expansion targets:

“….we [Figma] actually don’t have a customer success team. Everyone in the sales org owns a quota, and so if you’re post-sales on the account management team, you have an expansion target as well as a churning contraction allowance that you’re working towards.” - Kyle Parrish, Figma’s VP of Sales

How Figma built a $10B GTM engine 🎨 — At Figma, AM teams own expansion targets.

Navigate to the decision maker: Product-usage data when enriched and aggregated is rich with such intelligence as org hierarchies, decision making ability, and even data that’ll help navigate to the decision maker.

“Hey Brian, noticed that John and Paul from your team are using Toplyne. John’s recently brought Yoko onboard, and Paul’s already sent out an invite to Ringo. We think you could take advantage of our advanced security and SSO features. Let’s talk?” - Me, shooting my shot to the Beatles (c.a 1963)

Bottom-up messaging: As GitHub introduced top-down sales, the messaging now had to speak to three different personas at three different levels.

Individual developer - “Empowering a developer to work with other people to make better code faster.”
One level up - “Team communication platform, that enables conversations across teams.”
Further up - “Innovate in a large company at scale.”

Remove friction with content: It’s time for your PMMs to shine. Through customer customer-messaging and targeted content, your PMMs can warm up accounts for expansion and remove future friction from the expansion sale.

Work the deal in between meetings: Drift’s expansion teams multi-thread through LinkedIn, loop in legal, security, and compliance teams on Slack connect, and warm up to a call with the C-suite with a 5-minute intro-video made on Drift. Be like Drift.

And so in summary…

That’s a wrap on our three-part series on expansion.

Revisit part 1: What SaaS can learn about expansion from cats. Where we defined the extent of the expansion goldmine.

And part 2: What SaaS can learn about expansion from viruses. A breakdown of the best organic levers of team and account expansion we’ve seen in PLG tools.

When the market takes a turn for the worse, the “land” in “land and expand” becomes tougher than ever. Expansion’s the name of the game.