Podcast
August 1, 2025
Episode 52: RevOps Rewired
Mark Lerner explores how COVID, economic shifts, and AI rewired RevOps, focusing on platform consolidation and human-centered revenue operations.
In this episode of the RevOpsAF podcast, RevOps Co-op Founder and CEO Matt Volm sits down with Timmy Hendrickson, President of the Enablement Squad, to discuss one of the most consistently tricky challenges in RevOps and GTM orgs alike: change management. Specifically, Timmy breaks down how he successfully evaluated, deployed, and operationalized Seismic as a content enablement platform - and why none of it would’ve been possible without a strong partnership with his Revenue Operations team.
From outdated sales collateral and the lack of insights into content engagement to navigating internal pushback and stakeholder alignment, Timmy unpacks what it takes to introduce transformational technology in an organization that’s fast-moving, under-resourced, and battling enablement friction. If you’ve ever tried to roll out new tools or fix broken processes only to run into apathy or resistance, this episode is a tactical masterclass in cross-functional collaboration and driving real adoption.
Enablement is one of those functions - like RevOps - that suffers from a lack of universal definition. To eliminate ambiguity from the start, Timmy explains that enablement, in his view, means giving every customer-facing team - not just sales - the tools, knowledge, and assets they need to have high-quality, intelligent conversations. This includes everyone along the revenue cycle, from BDRs to customer success managers and post-sale support teams.
For Timmy, the ultimate objective is not just making people “look prepared,” but to empower them to influence outcomes: close more deals, retain more customers, and guide prospects through complex buying decisions. Enablement, when done well, goes beyond onboarding and training. It becomes a strategic lever to drive pipeline efficiency and downstream revenue metrics.
When Timmy joined HopSkipDrive in late 2023, he knew exactly what he was walking into - and it wasn’t pretty. The enablement structure was ad hoc at best, with sales reps using outdated materials buried in shared folders, and virtually no visibility into whether that content was useful or even accurate. Marketing teams were frustrated by the inability to connect their work to revenue impact. Sales leaders lacked data to know which assets actually influenced deals. And reps were essentially guessing what to send to whom, and when.
This “spray and pray” approach to content distribution was not only inefficient - it was risky. Important details were sometimes wrong, or irrelevant. Follow-ups lacked structure. Content performance couldn’t be measured, and there was no feedback loop to inform iteration or prioritization. Without enablement tooling, the entire revenue engine was flying blind.
Having built enablement functions at three different startups, Timmy brought a structured, experience-informed approach to tool evaluation. Rather than rushing into a vendor decision, he ran an internal discovery process that involved not just leadership, but frontline reps and veteran users. This helped him understand what the business truly needed from a content platform - and just as importantly, what it didn’t.
He created a vendor analysis matrix with defined success criteria, usability benchmarks, and integration requirements - especially with Salesforce, the company’s primary CRM. Each solution was reviewed collaboratively, with stakeholders adding feedback asynchronously before aligning in a group discussion. That inclusive process helped Timmy drive early-stage buy-in and defuse skepticism before it had a chance to grow.
Despite pressure from senior leadership to choose a more budget-friendly option, the team ultimately selected Seismic because it integrated tightly into their stack, required minimal workflow changes, and promised better long-term ROI. Timmy emphasized the importance of evaluating value over cost:
“It wasn’t the cheapest, but it was the most usable. A cheaper tool with low adoption is more expensive in the long run.”
One of the biggest factors behind the project’s success? Involving RevOps from the start. From evaluating vendors to coordinating integrations and setting go-live milestones, the RevOps team - led by the Director of Revenue Operations - was deeply embedded in every stage of the rollout. They helped build timelines, ensured compatibility with Salesforce, and scoped dependencies that would have otherwise caused blockers during implementation.
Together, Enablement and RevOps co-designed a three-phase launch strategy: design, develop, and deliver. During development, they ran a small-scale beta program with power users to test permissions, ensure data syncs were working, and debug usability quirks. This preemptive troubleshooting meant the full rollout landed with confidence, not chaos.
Even with a relatively small team (15 sellers and a handful of marketers and CS reps), Timmy emphasized the value of piloting first:
“If a feature breaks in front of 20 people, you risk trust in the entire tool. Fixing bugs before scaling it meant we didn’t lose credibility on day one.”
You should also check out our blog post How and Why to Hire an Enablement Professional.
A month after the launch, the question wasn’t just: Are people using it? The real question was: Is it working?
Timmy designed an ongoing reporting framework that connects Seismic usage to hard business outcomes: deal velocity, win rates, lead-to-opportunity conversion, and even average contract value. While traditional adoption metrics like active users are tracked, they’re treated as directional indicators - not end goals.
The insights have already paid off. Seismic data revealed that videos and one-pagers were consistently the most engaged-with content types. Meanwhile, long-form content like blogs and case studies lagged in terms of opens and time-on-page. Marketing now uses these insights to shape future content strategies - doubling down on high performers and eliminating low-impact assets.
“This gave us permission to say no to pet project requests that weren’t aligned with performance. Instead of building a 90-day case study, we can offer a 3-week turnaround on a high-impact one-pager.”
For more on this topic, check out our blog post Measuring the Impact of Enablement.
Before Seismic, reps often made off-the-cuff asks to marketing for new content - usually in the form of one-off requests like “Can we get a case study for this industry?” These requests, while well-meaning, weren’t grounded in performance data. With Seismic, Enablement now has evidence to validate or deprioritize those requests.
This shift created a healthier relationship between marketing and the field. Instead of reacting to anecdotal feedback, content teams now act on usage patterns and buyer engagement data. Sellers, in turn, are more strategic about what they ask for and when. And Timmy acts as a liaison between the two groups - ensuring marketing’s work gets used, and sales gets what it needs to close deals.
For more on this topic, also check out our blog post The Shift to Real-Time Enablement.
It’s no secret that in many early-stage or under-resourced companies, enablement duties fall squarely on RevOps. For teams without a dedicated enablement hire, Timmy offers this advice: prioritize relentlessly, and align everything to company outcomes.
“If you’re responsible for enablement off the side of your desk, focus on the things that tie directly to revenue goals. Not everything deserves a project plan.”
Matt echoed the point by emphasizing the importance of sequencing priorities to match where the business is in its growth stage. If your company is chasing new logo acquisition, focus enablement efforts on sales acceleration - not expansion or retention.
Together, they made a compelling case that enablement, when done right, is a force multiplier - but only when it's scoped thoughtfully and connected to metrics that matter.
Timmy’s story is a powerful reminder that successful change management is less about tools - and more about people, partnerships, and timing. His enablement rollout worked not because of a fancy tech stack, but because of structured collaboration with RevOps, a bias toward transparency, and a commitment to outcomes over optics.
It’s also a roadmap for other RevOps and Enablement leaders: if you’re standing up a new program, don’t do it alone. Bring in your cross-functional partners. Align early. Test small. And track what matters.
“You’re always going to have hiccups. But if you stay calm and lean on your RevOps team, you can build something that actually works - and lasts.”
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