Apr 27, 2023 · 47m · saastr
SaaStr CRO Confidential: Howard Lerman, Founder & CEO @ Roam | Founder-led Sales
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In this episode of CRO Confidential, host Sam Blonde interviews Roam founder and former Yext CEO Howard Lerman on founder-led sales, building a compound virtual headquarters, and executing contrarian go-to-market strategies.
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 5.3 Guest teaching 5.6 Guest disagreement 3.9 Jason pushing back 1.1
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 24:12 Cutting off the host to reject freemium
Howard directly cuts Sam off to vehemently condemn giving software away for free in B2B, dismissing conventional expert advice and attacking freeloader feedback.
Hardest push from Jason ▶ 21:57 Challenging perfectionism in shippingSam pushes back on Howard's heavy emphasis on seamless product experience, challenging him on how he avoids stalling releases in pursuit of perfection.
Biggest teaching moment ▶ 15:00 The faster horse rule for product designHoward delivers an authoritative critique of design-partner consulting traps, explaining why founders must extract problems from customers while ignoring their proposed solutions.
Jason holds their own ▶ 16:57 Sam demonstrates enterprise product incubation at BrexSam displays high domain expertise by drawing an exact operational parallel to how Brex's CEO spent months customer-facing to build Empower without building bespoke consulting features.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Closed Beta Metrics and Prioritizing Product over Growth | 4 | 4 | 3 | 1 | Sam frames the discussion around acquiring initial paying customers rapidly during beta. Howard immediately reframes the objective away from growth speed, emphasizing product polish and retention before general availability. | |
| The Genesis of Roam and Solving Distributed Work Friction | 4 | 6 | 4 | 0 | Howard gives an in-depth breakdown of enterprise communication friction, dismissing the debate over remote vs in-office work as juvenile. Sam agrees completely, citing his own experience at Brex and Founders Fund. | |
| Customer Zero Philosophy and Weekly Shipping Cadence | 3 | 5 | 1 | 0 | Howard details his customer-zero philosophy and shipping velocity of 56 weekly releases. Sam facilitates with standard timeline and interview probing questions. | |
| Organic Inbound Discovery and Customer-Problem Discovery | 7 | 6 | 4 | 2 | Howard rejects the standard design-partner consulting model, asserting founders must listen to customer problems rather than their proposed solutions. Sam demonstrates strong operator expertise by matching this with a detailed account of Brex developing Empower. | |
| Product Readiness, High Engagement, and Multi-Stage Testing | 5 | 5 | 2 | 3 | Sam probes how Howard balances product readiness against the need to ship without waiting for perfection. Howard explains their two-tier internal alpha and beta testing framework given high daily user engagement. | |
| Monetization Principles: Rejecting Freemium and Transparent Pricing | 5 | 7 | 7 | 1 | Howard aggressively interrupts Sam to denounce freemium models in B2B SaaS, warning against freeloader sample bias and the 'free monster'. Sam agrees and contextualizes the psychology of having financial skin in the game. | |
| Advisors as Enterprise BDRs and High-Impact Live Events | 7 | 6 | 5 | 1 | Howard rejects traditional junior outbound BDR programs in favor of leveraging senior equity advisors and high-ROI dinner events. Sam demonstrates deep sales leadership expertise by critiquing low-converting 22-year-old SDR email blast programs. | |
| Past Failures, Avoiding Dogma, and the Accidental Success of Group Tours | 7 | 6 | 5 | 1 | Howard details past product failures at Yext and warns founders against blindly adopting expert playbooks, citing how accidental group tours outperformed 1-on-1 demos. Sam validates this with practical examples from Brex and outbound campaign contests. |
Statements from this episode (17)
Lerman: Roam Bundles Multiple Apps Into an All-in-One Cloud Headquarters
“Rome is an all-in-one cloud headquarters. It makes companies more productive with fewer and quicker and faster meetings. It makes them more connected by bringing the company together, the entire distributed company together under one roof, and it helps save th…”
Lerman: Roam has 182 paying customers and 4,000 paid active members
“As of yesterday, when I last checked, we had 182 paying customers and about 4000 paid active members.”
Lerman: 100% of scaled companies are distributed
“Frankly, at Rome, we think that's all the wrong question because a hundred percent of scaled companies
Are distributed.”
Lerman: Roam has done zero marketing or outbound sales
“We haven't done any marketing and we haven't done any outbound. It's all just kind of been folks using the product.”
Lerman: Roam shipped 56 releases in its first 56 weeks
“And for the past, I guess, 56 weeks that we've been out there, we've had 56 different releases and, you know, continued to pack in improvements and features.”
Lerman chats directly with 50 to 100 Roam customers daily
“So I'm chatting with probably on the order of maybe 50 to 100 customers per on an average day.”
Lerman: Slack is weak at direct messaging compared to Roam
“We've added features for group chat that make it possible for a company to not, if they want, use Slack, because we think we have a better approach for direct messaging in particular, where Slack is pretty weak.”
Lerman: The average Roam customer uses the product 5.9 hours daily
“The average customer in Rome is in our product for 5.9 hours per day.”
Lerman: Free B2B software creates sample bias and bad feedback
“There is an enormous, and I've seen in my career, like over and over and over again, a huge sample bias when you give something away for free and freeloaders that have no intention whatsoever of ever buying anything, but they're glad to use your product for fr…”
Lerman: Freemium models force SaaS companies to compete with themselves
“If you do something freemium, kind of your, You're competing with yourself. You create the free monster where you've got this freemium thing, and then you spend a lot of time trying to come up with a differentiated feature that people are going to pay for, and…”
Lerman: Salesforce nixed Slack's monthly active user pricing model
“We went with monthly active users, which by the way is how Slack got started, But after the Salesforce acquisition, they nixed it. And so now you have to pay up front for the year and the kind of Salesforce more traditional sales model.”
Lerman: Senior advisors make better enterprise BDRs than junior sales reps
“The best BDR, the most, the best BDRs are the most senior people because they're a phone call away and can easily meet people and the board. And so I really think founders ought to think about how to construct their board and our advisors in a way that they ca…”
Lerman: Yext signed every gym by recruiting IHRSA's president as advisor
“In fact, when I started Yext, the very first thing I did, we were selling to gyms, and I called the founder and president of Ursa, which is the trade organization for gyms, and this was in And this is really old school. And he is now, you know, 78, 80, but I m…”
Lerman: Events are the highest-ROI B2B customer acquisition channel
“Events, I think are, The highest ROI way to reach customers in B to B. If you can, it doesn't have to be much. It's not that expensive to put on a dinner.”
Lerman: Yext's iBeacon product 'Zone' was his biggest career failure
“One of the biggest failures of my career was a thing called a zone at Yext. It was a product that Used a beacon. I don't know if you remember the beacons, the iBeacon protocol that Apple launched, that basically was this Bluetooth thing that could wake up your…”