Catch up on our Understory Unfiltered episode where Harris Kenny reveals how OutboundSync recovered a $400,000 Porsche deal and why agency partnerships beat direct sales for GTM.
Harris Kenny, CEO and founder of OutboundSync, built the data integration that connects modern outbound tools like Instantly, SmartLead, EmailBison, and HeyReach to CRMs like HubSpot and Salesforce. His solution has saved deals worth hundreds of thousands of dollars that would have been lost to attribution blindness.
Listen to this episode to learn how Harris transitioned from agency owner to SaaS founder, why he believes agencies are the future of GTM, and how taking user feedback seriously creates an engineering-to-revenue loop with zero dead features.
Harris Kenny is the founder and CEO of OutboundSync, the data integration layer connecting modern outbound tools to CRMs. Before OutboundSync, Harris ran Kenny Consulting Group (later Intra CRM), a tiered HubSpot partner agency where he was one of the first Clay experts.
His agency experience revealed a critical gap: modern outbound tools like Instantly and SmartLead prioritize deliverability over CRM integration, leaving growth teams unable to attribute pipeline to outbound activity. OutboundSync solves this by building pipes between systems, grafting limited data models from sequencing tools into the more sophisticated company, meeting, and deal objects that CRMs support.
[01:22] What OutboundSync actually does: building pipes between systems and why CRM integration matters more than UI
[08:44] Harris's transition from Kenny Consulting Group to OutboundSync and the agency struggles that sparked the idea
[12:25] The vision that paid off: why Harris bet growth hackers would move upmarket while legacy tools wouldn't adapt
[15:20] How OutboundSync builds features two to five years before mainstream buyers request them
[19:17] Why Harris personally vets every piece of user feedback without AI
[20:04] The engineering-to-revenue loop: zero dead features and every line of code tied to paying customers
[24:17] Why OutboundSync chose agency partnerships over direct sales and advertising
[26:42] How Slack channels and laser tag events build agency partnerships that reduce support needs over time
At Understory, we've retained multiple clients because OutboundSync revealed hidden attribution that clients couldn't see. In one case, a $400,000 deal with Porsche was about to be written off as a failure until OutboundSync data showed the prospect had received an email a week before booking a demo directly through the website.
As we discuss in the episode, this pattern repeats constantly: prospects receive outbound emails, never reply, then book demos directly and get attributed to organic traffic instead of the outbound campaign that actually influenced them. "They'll open it up at the contact level and they'll say, looks like you guys did send them an email actually. Like a week before we open the deal," Alex explains. At Understory, we've seen this happen at least three times where proper attribution tracking saved client relationships that would have otherwise churned due to perceived underperformance.
One of the biggest attribution mistakes we see at Understory is treating outbound as a silo focused on cost-per-email rather than as a hyper-targeted campaign with personalized messaging. As we discuss in the episode, people misunderstand outbound in critical ways: 2,000 emails might get 20 direct replies, but that ignores prospects who visit the website and convert via retargeting. Outbound hits the exact person, not just job titles or demographics, making it more personalized than most ad platforms.
Harris built OutboundSync because modern tools like Instantly and SmartLead prioritize deliverability over CRM integration. "These new outbound tools, they have like partial data models. They don't have company objects and meeting objects and deal or opportunity objects like the CRMs do," Harris explains. This gap is why OutboundSync has become a core component of our coordinated allbound approach at Understory.
At traditional SaaS companies, sales and marketing operate in silos where outbound sequences run through sales teams who write their own emails, creating inconsistent messaging. As we discuss in the episode, Understory exists to bridge that gap between sales and marketing, ensuring consistent messaging and brand identity across all touchpoints.
Harris's agency background gave him this same insight. He saw how disconnected systems created attribution chaos and messaging inconsistency. "My bet was that this way going to market, this growth hacking way would move upmarket and that the tools that could build these integrations wouldn't," Harris explains. The "pirates" in WhatsApp communities building growth-hacky solutions now serve mid-market companies asking about SOC 2 compliance, proving his thesis correct.
At Understory, Ali and Alex discuss this daily: when doing agency work, you play with so many different SaaS products that you learn where the gaps are and how to plug those holes. Harris's journey from Kenny Consulting Group to OutboundSync follows this exact pattern. He was one of the first Clay experts and a tiered HubSpot partner before identifying the attribution gap that became OutboundSync.
"I had this idea in the back of my head of like, have a service agency, solve problems, maybe identify a SaaS," Harris shares, referencing David Heinemeyer Hansson and Jason Fried from Basecamp as inspiration. The key difference between founders who make this transition successfully and those who don't: vision about where the market is heading, not just solving today's problems.
OutboundSync doesn't build for everyone. Their rallying cry is "helping winners win," focusing on being essential for the most elite operators in the outbound space. "I want to build gear for the astronauts and with the astronauts kind of thing. Cause like there's always another galaxy," Harris shares.
At Understory, we see this firsthand: Harris looks to our team to give feedback, and he believes features built for Understory will be features people request in two to five years. "I have prospects coming in. They ask me about features that I literally built two and a half years ago. And when they get on the call, they say, is this possible at all?" Harris notes. For SaaS founders, serving demanding early adopters creates a natural product roadmap.
OutboundSync generates revenue exclusively through agency partnerships, with no direct sales motion or advertising spend. "We're like riding with the agencies and it's like, we're going to live or die together," Harris explains. Their partnership approach treats agency problems as their own problems, providing unlimited support access across time zones.
At Understory, we've built our entire GTM engineering practice around tools like OutboundSync because of this partnership approach. "We don't measure our like number of tickets or ticket response time. We've never throttled someone's access to our team," Harris notes. This level of support lets agencies like Understory develop SOPs that reduce ongoing support needs while building predictable outcomes for clients.
The newest generation of outbound tools embrace data portability through robust APIs and webhooks. "Data is supposed to be free, right? So they build webhooks, they build APIs, they have them at all, then they're pretty performant and they're pretty well documented," Harris explains.
At Understory, we've built our stack around tools like Clay, Instantly, HeyReach, and OutboundSync specifically because they integrate seamlessly. When OutboundSync tries to integrate with larger enterprise players, they encounter resistance and poor documentation requiring complex workarounds. This philosophy difference explains why the GTM engineering space has consolidated around a specific set of interoperable tools, and why coordinated campaigns perform better than siloed channel execution.
Harris personally vets every piece of user feedback without AI assistance. He copies entire conversations into Trello tickets for engineering, records Looms explaining what users are trying to accomplish, and works directly with engineers to prioritize features. This approach has created an engineering-to-revenue loop where every feature ships to paying demand.
"I don't think our engineers have ever written a line of code that's not contributed to revenue. We don't have dead features in the product," Harris notes. At Understory, we've seen this responsiveness firsthand through our Slack channel with OutboundSync. As Alex observes in the episode, "You're taking user feedback directly from there and you're giving out basically the product in beta and saying, figure out what's wrong, tell me what's wrong. And you guys fix it immediately."
While OutboundSync's core function sounds simple: moving data from outbound tools to CRMs, the actual engineering involves solving dozens of edge cases. Webhook payloads can arrive too quickly, forcing the system to scale dynamically. Payloads can exceed size limits, like the 15-megabyte payload that broke delivery when it included a golf tournament graphic. Required IDs might be missing entirely.
"There's so many things in that basic assumption of I'm going to get a webhook payload, I'm going to receive it, and then I'm going to log an API call. There's so many things that can go wrong there," Harris explains. At Understory, we've seen clients try to build attribution tracking in Zapier only to return when real-world edge cases break their DIY solutions. Proper infrastructure investment pays for itself when it prevents attribution blindness on six-figure deals.
Want more insight on outbound attribution and GTM infrastructure? Listen to the full episode on YouTube and subscribe to Understory's podcast for more insights on coordinated campaign execution.
Looking to eliminate the attribution gaps in your outbound program? Book a call with Understory to explore how coordinated paid media and GTM engineering can connect your outbound activity to pipeline.
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