Strategic Growth and Acquisition with Dean Dutro of Worth eCommerce
Key Takeaways
- Dean's first email marketing client paid $900. The first flows made $15,000 to $20,000 a month within weeks, and that became Instant Email Copy.
- Before growth hit, Dean sketched org charts for 10 and 20 more clients, and he says the recruiting pipeline needs to be as strong as the sales pipeline.
- Worth's job posts lead with the company, culture, and values and don't mention the job until later. Remote roles that pay well draw 100 to 200 applicants.
- $10,000 to $20,000 a year on the Jason Swenk mastermind came back as roughly 10 closed clients, a podcast, and the introduction to the M&A advisor who ran the sale.
- Dean's four salespeople sell for about $12,000 what he used to sell for $1,500. His regret is not hiring salespeople five years earlier.
- Moving from cash to GAAP accounting in due diligence meant revenue Dean expected to keep went to the buyer, and untracked PTO had to be paid out. After closing, the team tried to change too much at once.
Dean Dutro is the co-founder and CEO of Worth eCommerce, an email and SMS marketing agency for ecommerce brands built on Klaviyo. Gray MacKenzie hosted, a few months after SmartBug Media acquired Worth in 2021. Dean told the story in order: a first agency that went into debt, the $900 project that became an email business, the merger that created Worth, and what tripling and then selling did to him and the business.
A $900 project that became the business
At 24 or 25 Dean was selling to Boeing and other aviation companies when his friend Ryan, a UX designer with a small agency, asked him to join and handle sales. Their first company, GobySavvy, traveled through Asia, Europe, and Australia and “did everything except for the make money part.” A year in they were in debt and living with their grandparents. Ryan moved into ecommerce work, and a client, Koala Mattresses (“the Casper of Australia at the time”), asked whether they did email marketing.
I was like, yeah, we do. I’d never done it before. And we charged them $900, which is a ridiculously cheap amount for what we provided. But I took a week and I learned everything about… copywriting, design, email marketing… And the first automations or flows we set up for these guys, within weeks we’re generating like 15, 20 grand a month. I was like, I think we could sell this. And so I started Instant Email Copy.
Two competitors who merged instead
Ryan eventually started selling email marketing too.
He started competing with me and doing email marketing. I was like, what the hell, man. But there’s so many clients, it was like neither of us could fulfill on the amount of clients that were coming in… We spent two weeks in Bend, Oregon, which is my hometown, and came up with Worth eCommerce. We created a list of values that we wanted to live by and hire people by… created a mission. And that was a big turning point for us.
That was September 2019, with about 15 people between the two businesses; at the sale two years later, Worth had 45. The founders also swapped roles once they saw each other work: Ryan took growth, and Dean, a former recruiter, took CEO and operations.
Sketch the org chart before you need it
Gray asked what Worth got right to triple in two years. Dean’s answer was preparation.
I would literally just write down on paper, I would create an org chart, and I would sketch it out and say, okay, if we gain 10 more clients, what does our company look like? If we gain 20 more, what does it look like?
His years as a recruiter meant he also built a recruiting pipeline, which he thinks most owners skip: “if you optimize sales, you need to have people to fill in the work.” Worth moved to almost all employees because contractor costs add up at scale, and its job posts draw 100 to 200 applicants because the roles are remote, pay well, and the post covers the company, culture, and values before it gets to the job.
Paying for outside help, and hiring salespeople sooner
Gray noted that Dean invests in outside help more readily than most owners. Dean put a number on the Jason Swenk mastermind.
Maybe I’m paying X amount per month and spending 10 to 20,000 a year on mentorship, but from that mentorship, in that group of people, we probably closed 10 clients, which is worth hundreds of thousands of dollars. We got a podcast started… It’s like a 20,000 investment has turned into a 10x, 20x return… That is the best ROI I’ve ever seen.
A near-six-figure sales system build with Joey Gilkey paid off too; some lead gen agencies he paid never delivered. The bet he wishes he’d made sooner was hiring salespeople.
My salespeople, we’ve got four salespeople, and they’re selling a product that I used to sell for 1,500 for like 12 grand. And it’s literally the same thing… I don’t think I would have ever been able to sell it for that. My skills aren’t there… When they did that, I was like, I should have hired salespeople five years ago.
What due diligence and GAAP did to the deal
Dean reached out to M&A advisor Todd Taskey (a referral from the mastermind) mostly to learn how acquisitions work. Todd said Worth was probably too early, and the process took about a year. SmartBug’s team had a clear path for what Dean wanted to do next, go from 50 people to 500, and the model matched: HubSpot and B2B for them, Klaviyo and B2C for Worth. He was 30 when he sold. Due diligence “sucks,” nobody is ready for it, and deal fatigue had him convinced the Friday before signing that it wouldn’t close. The business suffered for a few months, and the accounting surprised him.
Going from cash accounting to GAAP accounting… there’s revenue that I thought would go into our pockets that actually went to the company, because of the way GAAP accounting works, revenue isn’t counted until the work is fulfilled. So all that gets pushed, so you actually end up sometimes having to write a check to the company that purchased you for that weird period of revenue.
Untracked PTO was another one: the buyer works out a percentage and the seller pays it out. Then came the post-close urge to fix everything.
We were all gung-ho about, we’re gonna change stuff up… and with this whole spreadsheet of stuff and action items, it was too much. You don’t realize how hard it is to change a system. And so we finally had to have a conversation and say, hey, we need to go back to our core focus and competency.
The rest of the episode covers Q4 seasonality (upsells, not new clients), Dean’s Relationship Commerce podcast at nearly 100 episodes, and his note that the ClickUp system ZenPilot built for Worth gets used every day, even if not everyone follows it.