Why Agencies Must Lead With Strategy (Not Just Execution) With Pete Caputa | Ep #835

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Are you stuck acting like an order taker instead of leading your clients with strategy? If you want to grow an agency that survives the competition, you need to do more than deliver pretty websites or manage ad budgets. You need to lead with strategy, prove it with data, and guide your clients through the journey—not the other way around.

Too many agencies are still making decisions based on “gut feelings” instead of data, which is why today’s featured guest is tackling exactly that problem—making it easier for everyone in a company to use data daily, so decisions are grounded in reality, not instinct.

Pete Caputa is the CEO of Databox, a business intelligence platform built for small to mid-market companies that makes data adoption simple across teams. Before that, Pete spent nine years at HubSpot, where he famously launched and scaled the agency partner program—now responsible for billions in revenue.

But Pete’s journey didn’t start in SaaS boardrooms. He began as an engineer, dabbled in early 2000s web apps after learning to code, and struggled through the grind of bootstrapping. his own ventures. A key pivot came when he connected with sales coach Rick Rober, who helped him sharpen his sales chops. That path eventually led him to HubSpot as the fourth sales rep and later, the architect behind the company’s groundbreaking agency channel.

In this episode, we’ll discuss:

• Creating the HubSpot Agency Partner Program.

• Why agencies need to lead with strategy.

• AI as the new strategic edge.

• Selling strategy as a service.

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Early HubSpot sales conversations looked familiar to many agency owners: lots of free education, lots of excitement… and lots of ghosting. Agencies wanted to roll HubSpot out to their clients, but deals rarely closed. Pete recognized the deeper problem —agencies were stuck in project-based work and living on the cash flow rollercoaster.

So he set out to teach agencies to package ongoing retainers instead of chasing one-off projects. That simple but powerful shift unlocked stability and scale. Agencies suddenly had recurring revenue, longer-term client relationships, and the ability to deliver compounding value. HubSpot, of course, became the backbone of that service delivery. What started as a scrappy idea became a multi-billion-dollar channel—and one of the most successful agency programs in SaaS history.

As HubSpot scaled, so did its internal politics. Pete found himself in the middle of a growing conflict between the direct sales team and the partner channel. Instead of collaborating, the two operated like competing businesses, often clashing at the deal level.

Pete saw a solution, but realized implementing it would be painful in company scaling that fast. He eventually stepped away, even though he was responsible for nearly 40% of HubSpot’s revenue at the time. “It got harder to get things done,” he admitted—proof that what works in a startup culture doesn’t always survive as companies mature.

Back in the early 2000s, agencies had to convince clients digital marketing was worth investing in. SEO, social, and funnels were foreign concepts for most businesses. Agencies had to sell belief before they could sell retainers.

Today, the problem isn’t buy-in—it’s competition. Businesses now see digital as essential, but agencies are often commoditized into executing tactics. Instead of being trusted advisors, many find themselves replaceable—either by freelancers, in-house hires, or other agencies that “do the same thing cheaper.” The risk is clear: if you’re not leading clients strategically, you’re just a vendor waiting to be swapped out.

Most agencies claim to do strategy, but really, they only use it to justify selling a tactic. Redesigning a website? They’ll run some quick competitor research. Launching content marketing? They’ll whip up a persona doc. But that’s not strategy—it’s sales collateral.

Pete is now working on a framework he calls Predictable Scale. It starts with true strategy: competitive research, customer research, defining vision and mission, and setting clear objectives. Only then do tactics come into play. Most agencies don’t put these together in the right sequence and, as a result, get pushed in to executing tactics. For agencies, this is the key to breaking out of the execution box and earning a permanent seat at the table.

These days, agencies can leverage AI to accelerate strategy and client service. It can be as simple as using AI to run a SWOT analysis, refine your brand voice, mission and vision, and then taking all the data and use it to create a custom GPT you can run to generate client-facing plans. One mastermind member, Chris Dwyer, took this to the extreme by building a board of AI advisors (finance, marketing, sales, and acquisitions) and saw incredible growth as a result.

Pete’s team has also dabbled in this use of AI and created a custom GPT called Pete GPT. They feed in customer interviews, surveys, and Pete’s own writing so the tool can generate content in his voice.

Beyond content, AI is speeding up product feedback loops. By connecting call transcripts, chat logs, and support tickets, his product team can instantly spot customer needs and prioritize features—a process that used to take weeks of interviews. Pete also has an AI agent that handles about 50% of his agency’s conversations with prospects and clients, with a customer satisfaction score of 70% so far. For agencies, the message is clear: if you’re not already embedding AI into your workflows, you’re falling behind.

Not everything should be automated, however, especially when it comes to onboarding. Onboarding can make or break a client relationship in the first 60 days. Too many agencies rely entirely on Zoom and automation, missing the opportunity to build true connection. “No one meets with clients in person anymore,” he said, and it’s costing them.

Some of the most successful agencies in Jason’s mastermind make it a priority to visit new clients in person during the first quarter. That small gesture builds trust, creates deeper bonds, and makes it much harder for clients to churn later. With competition as fierce as it is, going the extra mile in onboarding may be the simplest competitive advantage agencies can claim.

Pete wrapped up the conversation by introducing Databox’s new program for agencies: business intelligence as a service. Until now, most agencies used Databox to report on campaign performance. But Pete sees a bigger opportunity—helping agencies package BI consulting as a strategic service.

Instead of being the vendor that just improves ad ROAS or runs SEO reports, agencies can step up as partners who improve an entire company’s performance. That means quarterly reviews looking not just at marketing metrics, but at sales, ops, finance, and customer success data too. For agencies tired of being “order takers,” this is the chance to finally sell strategy over tactics—and get paid for it.

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