From Community to Capital
In this powerhouse episode, Max Altschuler - founder of Sales Hacker, former VP of Marketing at Outreach, and now General Partner at GTMfund - breaks down what it takes to build and scale B2B SaaS companies with speed and substance. Max shares his journey from being an early-stage operator to becoming a SaaS investor, unpacking the real mechanics behind GTM strategy, community-driven growth, category creation, and what founders often get wrong. This is a masterclass in strategic execution and long-game thinking for SaaS leaders.
💡 Insight #1: Great Founders Ride Great Waves
“You can have the best surfer and the best board, but without a wave, you’re going nowhere.”
Early-stage bets are 90% founder, 10% space.
But even a killer founder can’t defy market gravity—Max only invests when both the founder is relentless and the market is expanding.
His investment in Outreach? Manny Medina was “a machine” obsessed with customer input, had product DNA, and was solving a real emerging need—sales engagement.
🧠 Insight #2: Media Is Your Moat
“We weren’t buying Sales Hacker for revenue. We were buying it to compound Outreach’s value.”
Sales Hacker wasn’t a media asset. It was a distribution engine—strategically neutral, but subtly influential.
Outreach resisted the urge to blast its messaging. Instead, it used Sales Hacker to shape category conversations and build trust.
Strategic move: Acquire attention, not just leads. Outreach’s dominance in the sales engagement category was fueled by this subtle but sustained media-driven halo.
🧱 Insight #3: Category Creation Is an Execution Sport
Outreach didn’t just sell tools. It owned the narrative.
Max’s team bought the domain salesengagement.com, launched a book, a podcast, and drove education on the category—not just the product.
This approach helped Outreach go from $25M to $250M in ARR, outpacing competitors who were purely feature-selling.
🛠️ Insight #4: Playbooks Age, People Compound
“My biggest regret? Not paying up for talent earlier.”
Early Max was frugal on hiring. Mature Max hires killers and lets them run.
Great operators don’t cost money—they generate it.
Investing in A+ talent early delivers asymmetric upside. Your first VP hire can be a 10x unlock—or a 10-month delay.
🏗️ Insight #5: Don’t Just Build—Buy Wisely
“We waited too long on acquisitions—missed the data game, missed the Gong window.”
Outreach was biased toward building. That cost time and missed strategic windows.
Lesson: When the timing is right and tech is cheap, move fast. Distribution > perfection.
Max sees missed M&A as one of the few strategic missteps in Outreach’s scale phase.
🎙️ Tactical Gem: Podcasting as a Sales Trojan Horse
“Want a Fortune 500 exec’s attention? Invite them to talk—not listen.”
Outreach’s Sales Hacker podcast wasn’t content marketing. It was outbound disguised as value.
Max booked execs sales couldn’t reach, built rapport through interviews, then opened deal conversations.
Lesson: Stop cold emailing. Start offering platforms.
🧭 Final Takeaway: Now Is the Best Time to Build
“2015 had no Cursor, no Sales Hacker, no resources. Today, anyone can build with leverage.”
With AI, abundant GTM knowledge, and investor-operator communities like GTM Fund, the excuses are gone.
Max’s advice: Build with obsession. Hire elite talent. Control your distribution. The rest will follow.
