Jan 2, 2019 · 41m · saastr
Going Upmarket, How To Keep Growing When Your Buyer Is No Longer Your User
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
At SaaStr, Accel Partner Vas Natarajan and UserTesting CEO Darrell Benatar outline actionable strategies for SaaS companies transitioning upmarket to sell enterprise platforms when the economic buyer is no longer the daily end user.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 5.2 Guest teaching 2.4 Guest disagreement 1.4 Jason pushing back 0.8
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 35:10 Playful jab at InVision security limitations
Darrell playfully points out that InVision failed a customer's security requirements, prompting UserTesting to build the hosting feature and win the testing workload.
Hardest push from Jason ▶ 24:36 Warning against early sales rep hiringVas strongly advises founders not to rush into hiring expensive enterprise reps before learning how to close the accounts personally.
Biggest teaching moment ▶ 7:21 Risks of service differentiation ahead of product maturityDarrell breaks down the trap of relying on managed services to bridge enterprise value gaps before achieving full product feature maturity.
Jason holds their own ▶ 16:42 Differentiating executive ROI from practitioner speedVas synthesizes enterprise messaging architecture, showing how executive buyers require business agility narratives compared to ICs seeking speed.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Transitioning to Enterprise and Packaging Service Differentiation | 6 | 2 | 1 | 1 | Vas Natarajan introduces SaaS benchmarks around $1-2M ARR transitions and frames the discussion around enterprise pull versus push. Darrell shares the foundational story of packaging managed services to satisfy early enterprise budgets, maintaining a collaborative and reflective tone. | |
| Selling to Executive Buyers Versus Frontline End-Users | 5 | 3 | 1 | 1 | Vas brings comparative board-level experience from InVision regarding marketing to CXOs versus frontline practitioners. Darrell elaborates on the discovery process and tactical ways to leverage internal champions without antagonizing executive decision-makers. | |
| Structuring Enterprise Sales Teams and Founder-Led Selling | 6 | 2 | 2 | 1 | Vas emphasizes the critical role of founder-led selling for technical buyers before hiring dedicated enterprise account executives. Darrell jokingly teases Vas that this advice arrived too late before breaking down the necessity of solutions consulting teams. | |
| Product Readiness, Technical Debt, and Managing Roadmaps | 5 | 3 | 2 | 1 | Vas warns about larger buyers treating early startups as outsourced R&D. Darrell playfully calls out InVision's hosting security shortcomings while explaining how UserTesting disciplined its enterprise roadmap commitments. | |
| Balancing Self-Serve Origins with Enterprise Growth | 4 | 2 | 1 | 0 | Vas asks how UserTesting balances internal tensions between low-end pay-as-you-go offerings and enterprise growth. Darrell explains the persistent price-anchoring challenge of their $49 tier as an essential lead generation engine. |
Statements from this episode (12)
Enterprise Inbound Interest Typically Begins at $2M to $3M ARR
“It tends to be around the two to three million dollar mark where you're getting larger logos that are starting to knock on the door. The enterprise pipeline is starting to swell”
Moving Upmarket Requires Product Maturity and a Scaling Value Metric
“If you're gonna start down market and move up market, you need to have the product maturity to justify the pricing difference, and pricing becomes a challenge. You need a value metric that scales”
Enterprise Sales Require Slow Discovery Rather Than Transactional Demos
“When we're selling to an SMB, it's very transactional. It's about demoing the tool and demonstrating utility. When you're selling upmarket, you are you have a selling process where you want to slow things down and go through a process of discovery.”
Six-Figure Enterprise Deals Often Close Without Showing Executives the Product
“It's not untypical for a salesperson selling a large six-figure deal to never show the product. To the executive they're selling to.”
Six-Figure SaaS Deals Require Experienced In-Person Field Selling
“The reality still stands that you kind of have to do a lot of in-person selling if you're going to be selling six-figure deals into large companies and you're hiring, ah, you know, a more experienced rep who has the sophistication to, ah, ask the right questio…”
Founders Should Close Initial Enterprise Deals Before Hiring Sales Reps
“One of the learnings I've seen is don't rush out too quickly to go hire the expensive enterprise sales reps. Learn how to sell those early enterprise deals yourself. Cause it is illuminating from a product marketing sales support and success standpoint.”
Meeting Enterprise Security Requirements Creates a Competitive Moat Against Startups
“The good news is, is that, ah, that's a requirement for selling into these companies, and it becomes a competitive differentiator After you've invested that time in it, so the other little startups are coming along, they, they're gonna have to go through that …”
UserTesting Only Pulls Planned Roadmap Features Forward for Major Accounts
“When we think about, you know, that issue of large startups wanting you to do special things that maybe weren't on your roadmap, whatever we've been pretty disciplined about that, and the policy is, if it's something that's pretty close to something that was, …”
Enterprise Client Tested InVision Through UserTesting Due to Security Flaws
“I think one of the last one that we did was secure prototype hosting, because the, this company that we were dealing with Envision's hosting did not meet their security requirements. Uh-oh. And we did. So they now test all Envision through user testing.”
Enterprise Customers Understand When Ambitious Long-Term Product Roadmaps Change
“Get to a kind of a level of trust where, ah, we could put out that, ah, roadmap and understand that, you know, some of the things that are further out aren't gonna happen. It's gonna change and, ah, believe that customers are gonna understand that. They're not…”
Enterprise Drives UserTesting's Revenue Growth, Not Customer Count
“Enterprise is, you know, the fastest growing part of our business in terms of revenue, not in terms of customers”
UserTesting Keeps $49 Tier for Leads Despite Sales Price Anchoring
“We still have a 49 dollar pay-as-you-go offering, which creates price anchoring problems for the sales group, and we continue to look at how we can evolve that. So that, you know, there's, that's less of an issue, but it's always been a great source of leads f…”