On this episode of Revenue Mavericks, I sat down with Anna Osborn, Chief Revenue Officer at Blackbird.AI. Anna has been working since she was 9 years old, and that's not a figure of speech. From babysitting and selling Girl Scout cookies in a tiny town in northern Michigan to leading revenue at a category-creating narrative intelligence platform, the throughline of her career is the same: figure it out yourself, and start before anyone tells you you're ready.

1. $25 and a Ten-Speed Bike

Anna grew up in a household where finances were a constant source of tension. She watched the imbalance between her parents and decided early that she never wanted to depend on someone else for financial security. So at 9 years old, she started working. Mother's helper jobs, babysitting, riding a ten-speed up and down hills to get to the next family who needed her.

She remembers the first week she got a check for $25 and feeling like everything was falling into place. From there, the jobs kept expanding. She sold Girl Scout cookies, spaghetti dinner tickets for ski team, pumped gas into boats during the tourist season. Each one taught her something different about how businesses worked, what made people buy, and what happened when you showed up consistently.

What made those years distinctive wasn't just the work ethic. It was what she did with the relationships. Through her nannying jobs, Anna opened doors to experiences she never would have had otherwise, including traveling internationally for the first time at 14 and working at the Sydney Olympics. She wasn't networking in any strategic sense. She was just showing up, being reliable, and paying attention. The opportunities followed.

That pattern carried straight into her professional career. She talks openly about knowing her strengths and weaknesses well, and says she talks more about her weaknesses than her strengths because that's how she knows where to build her team. The instinct to self-assess, to figure out what she's missing and go find it, started with those early jobs.

2. The File on the Table

The most formative experience of Anna's professional career wasn't a promotion or a big deal. Rather, it was getting fired.

Earlier in her executive career, Anna joined a company and tried to make changes she felt strongly about. The leadership team was applying what she describes as a rinse-and-repeat template, and she didn't think it fit the company's stage. She pushed back hard. And for anyone who's worked with Anna, that's a defining characteristic.

It wasn't well received. Around the time she had her second daughter, she went out on maternity leave. When she came back, her boss walked into her office one day and asked her to step into another room. She opened the door and saw the HR person sitting at the table with a file. She knew immediately what was happening. And then she was escorted out by security.

It was jarring. Anna says she had never experienced imposter syndrome prior to that point in her career. She'd had plenty of it in motherhood, but professionally, never. The firing cracked that open. She started questioning everything: what it said about her, whether she was actually as good as she thought she was.

But what came out of it reshaped how she approaches every role since. She realized that her most authentic professional self isn't for every company and it's not for every stage of every company. And rather than being limiting, that realization was freeing. She tells people coming up in their careers to get fired early, because once you've survived it, you can bring your authentic self to work without being paralyzed by the fear of losing the job. You stay sharp because you want to, not because you're afraid.

3. The Case for Diabolical Focus

When Anna talks about what separates the startups that win from the ones that stall, she keeps coming back to one word: focus.

In resource-constrained environments, she says, every new product that gets thrown over the fence requires a level of bootstrapping that most teams underestimate. A small product team is responsible for everything, and when the next thing gets added before the current thing is finished, the cascading effect touches every function. Sales teams are trying to build pitches, learn the product, articulate value, and develop onboarding processes all at the same time, and suddenly the organization is being asked to do it again for something new before any of those muscles have been built.

The companies and functions she has seen win are the ones that are, in her words, diabolically focused on committing to getting a product or service to a certain point before moving on to the next thing. Nothing is ever truly done, she acknowledges. But the discipline of finishing before starting is what allows a constrained team to actually build competence rather than spreading thin across half-built capabilities.

Why This Matters

Anna's story is a reminder that the best revenue leaders aren't always the ones with the smoothest career arcs. Sometimes the most important thing that happens to you is the thing that knocks you down, because it forces you to figure out who you actually are when the title and the office are gone. Anna figured that out, and it made her more fearless, not less.

She also brought something to this conversation that I think about a lot in the context of building Terret: startups don't fail because they lack ambition. That, they have plenty of. They fail because they try to do everything at once. The discipline of focus, of finishing the thing in front of you before chasing the next opportunity, is one of the hardest lessons in early-stage companies and one of the most valuable.

Listen to the full conversation on the Revenue Mavericks podcast.