He Spent $50K a Month on Outbound That Failed, Then Fixed It

Where He Started

Chris Dreyer was a detention room teacher. Detention room teachers, as he tells it, do not get paid very much, so on the side he was an affiliate marketer, “slinging everything on Amazon, ClickBank, CJ Advertising.” Within a couple of years the side income was four times his teaching salary, which was enough of a push to go all in.

Then Google’s first Penguin update hit. About half of his backlinks were Ezine article links, “because they just worked back in the day,” and his income dropped. He went to Craigslist looking for a job and got three offers from three different agencies. Most people pick one. Chris accepted all three, ran them with a team of eight people in the Philippines he already had, and became the best-performing contractor at all three agencies at once. That is how he learned the agency business before he ever started his own.

When it came time to pick a niche, he chose legal, and specifically personal injury, on purpose, not because it looked easy. “I want to go where the red ocean is,” he says. “Like where is the war happening? There’s a reason why the war is happening there, and it demands expertise, so I want to go right into the battle.” He went general legal first, then narrowed hard to personal injury for years, referring out anything that did not fit. A personal injury marketing book, a personal injury podcast, personal injury case studies, and his own personal injury conference, Pimcon, all followed from that one decision to go deep instead of wide.

The $10 Million Ceiling and the Outbound Mistake

The first ten million was built almost entirely inbound: events, Google Ads, social media, Facebook ads, referrals, and content, all of it aimed at building enough trust and authority that attorneys came to him pre-sold. Chris calls that period “hoping and praying that a good client comes in.” It worked, but it capped out. “From five to ten was really hard,” he says. “We scratched and clawed to get to ten million.”

To break past it, he decided to build an outbound engine, and his first move was to outsource it. He hired a well-known outbound sales agency, eight SDRs at once, for about $40,000 a month, specifically so he would spend enough money and move fast enough to know whether it worked. It did not. New reps would just start to understand his ICP and messaging, then get promoted off his account. He never controlled the list of who was actually being contacted. And the incentive structure was backwards: reps were paid per appointment booked, so they booked appointments, not fits. “I’m not gonna name the company,” he says, “but here’s what happens.”

He tried a second outsourced vendor at roughly $50,000 a month for several more months. Same result. Everything changed only when he brought it in-house.

Building the In-House Machine

Instead of hiring individual reps himself, Chris hired a recruiter with one mandate: find a VP of Sales who had already built a successful outbound team and would bring people with him. The VP he hired brought his best friend, a former head of outbound at another company, and from there the team filled out with a bench of former President’s Club winners.

The structure now runs on a defined career path: BDR, senior BDR, key BDR, then AE1, where a rep shadows one account executive on every call and proposal before being promoted to a full senior AE with BDRs feeding them appointments based on calendar capacity. Compensation is built to reward the right fit, not just the close: BDR base pay runs $60,000 to $75,000 with an on-target total above $100,000, and account executives have a minimum OTE of $200,000, paid as 10% of the retainer spread over the client’s first six months. If a client churns in month two, the rep only gets paid for the two months the client actually stayed.

The team is held to metrics that favor quality over volume: 50 quality dials a day, not the 100-plus some outbound shops push, tracked on a weekly leaderboard Chris calls the “internal Jumbotron.” Every call is recorded and reviewed, reps go through a two-week boot camp plus ongoing outside coaching, and every one of them gets certified through outside SEO training so they can actually speak the language of the service they are selling.

Chris is just as clear about where the standard gets enforced with pain attached. His best BDR earned a promotion to account executive, then missed quota in the new role. His head of sales asked whether to move him back to BDR. The answer was no.

He also let go of a top account executive he genuinely liked, “a killer,” because the person never bought into outbound and kept working against the direction the company needed to go. “It’s the people who got you there won’t get you here,” he says. Both decisions still bother him, and he still made them.

Where He Is Now

Rankings.io is on pace to hit $34 million this year. The team, including contractors, is around 150 people, fully remote, running on Slack, Notion, and ClickUp, deliberately hired in regional pockets so people can still meet in person. The client roster sits around 220 law firms, served by an outbound team of about 20 salespeople working alongside the original inbound engine of content, podcast, and conference that got the company to its first $10 million.

Chris now treats sales and marketing as one blended revenue function rather than two departments, and he is applying the same playbook, book, podcast, conference, deep focus, to a second vertical in criminal defense rather than resting on personal injury alone. His closing advice to an agency owner still stuck at the first plateau: “The individuals with the highest standards often win. Set your standards higher.”