Support Ticket to CEO, No Job Hopping: A Conversation with Margaret Sikora

Most CEOs either found the company or parachute in from outside with a fancy resume. Margaret Sikora did neither. She started at Woodpecker in 2017 as a junior customer success specialist answering support tickets, and over eight years climbed to customer success officer, head of support, interim manager, head of product, COO, and finally CEO, without skipping a step or hopping companies every 18 months. She also earned a PhD in law somewhere in between. She lived every part of the business, and Woodpecker kept promoting her.

What makes Margaret worth listening to is that her whole worldview was built from the ground floor up, so she talks about leadership, hiring, and cold email from lived experience rather than theory. This conversation is about how you go from support tickets to CEO, managing people who used to be peers, and what actually changes when the title becomes yours.

From support to product to the top

Margaret did not plan the climb; she was looking for a summer job during her law studies and fell for Woodpecker's five-person, early-stage spirit and the entrepreneurial B2B-sales niche. What kept her was learning the technology, working with the CTO to help customers efficiently, because understanding how the product actually works is a different level of engagement. Her move into product was organic: customer success people burn out, she argues, because they take all the mess from customers but cannot change anything, and if the company was going to succeed it needed to stay close to those customers, which is the natural bridge to product.

She resists comparing herself to other CEOs, since every story is unique, but she is clear that for a niche like B2B sales, being a CEO from outside the business is extremely hard, and that a team is more motivated by a CEO who has done the work alongside them. Selling to salespeople, she notes, is not about a slick pitch, because half her clients pitch better than she does; it is about delivering value and speaking their language of conversion and leads. Her leadership style comes down to honesty (she is not politically correct, because people see through it) and fairness (being able to look in the mirror), plus a genuine belief in hard work and repetition to master a skill.

Hiring, imposter syndrome, and letting go

On imposter syndrome, Margaret has a grounded reframe: there is an organization, an amount of work, and a set of people including her, and she does not care which of those people does the work as long as it gets done. The questioning voice is always there at every level, but the role does not validate the skillset, and being CEO is a side effect of helping the company grow, not the gist. She learned hiring the hard way, early on trusting the feeling that someone was a good fit, which led to homogeneous teams of people too similar to each other. Now she leads with the objective question of what KPIs and deliverables a person should bring, so she does not burn a great player's career on absent expectations.

Letting go of roles she loved was genuinely hard, since she is sentimental about her jobs and was sad leaving both support and product. What made it possible was seeing people better than her step into those seats, and trusting a self-sustaining team or a leader she believed in, because wearing five hats means doing none of them as well as a focused specialist. The transition from COO to CEO changed her day-to-day a lot: far more PR, external communication, and LinkedIn presence, and a shift in optic, because a manager brings solutions up to a superior, while a CEO has no one to appeal to and must let people do things differently than she would.

It's lonely at the top, and burnout is a choice

Margaret confirms the top is lonely and navigates it with a strong C-level and board she can talk ideas through with, plus the acceptance that you do not delegate responsibility: all failures are hers, wins are the team's. Her guard against taking it personally is to remember it is the story of a career and a company, not of her personally, because internalizing it leads to burnout that brings no results. And she claims, strikingly, that she is not even close to burned out, which she attributes to treating her own energy as an investment she is responsible for generating, through exercise, travel, and a love of cold places like Svalbard, Greenland, and Alaska.

On the "no my project" mindset, she is firm that projects belong to the company, not to the people who championed them, so shutting down a product is a business decision and never a judgment of the person who pushed it, because every successful company has a graveyard of ideas it tried and withdrew. She also shapes the market by not doing things, resisting the two-month fads (the gimmicky cold email with your name on a picture of a cup) even when they are fashionable, because a good product is defined as much by what you refuse to build as by what you ship.

Cold email isn't dead, and advice you should ignore

Woodpecker competes in a crowded cold-email market, and Margaret's edge is being multichannel now (email plus LinkedIn) and building for safety, so the system does the heavy lifting on deliverability, with free built-in email validation and full database separation for agencies. To anyone who says cold email is dead, her answer is that every channel is dead if you do not know how to use it, the same as cold calling, paid ads, or trade shows; if you can monetize the channel, it is good enough, and if you cannot, you can complain or learn. What has actually changed is the tech, from vertical sending (one mailbox, one domain) to horizontal (many mailboxes and domains), and spray-and-pray volume that dropped roughly 12-fold for one big client over four years, replaced by microsegmentation and better targeting.

Her closing advice is the sharpest thing in the conversation, and worth taping to a wall: do not take advice from anyone. Select very carefully whose advice you allow in, because if the person is not in the position you want in life or is not someone you admire, ignore them. She heard many times that she was burning out her career and should switch, and she filtered it. And, echoing what other guests said, she does not believe in shortcuts unless you are born a genius, or in following passion, because passion and motivation are fleeting emotional bumps, while routine and discipline are what actually build success, the way you run on a training day rather than only when you feel like it.

Key takeaways

A few things worth keeping.

Get close to the product. Customer success burns people out because they absorb the mess without power to change it. Moving toward product, to serve those same customers, is the natural escape.

Hire for KPIs, not vibes. Trusting the "good fit" feeling builds homogeneous teams. Lead with what deliverables the person must bring, so you do not set a good hire up to fail.

Don't internalize the company. Projects belong to the company, not their champions, and the CEO title is a side effect of helping it grow. Internalizing it just leads to burnout.

No channel is dead. Cold email, like any channel, is dead only if you cannot use it. The tech shifted from vertical to horizontal sending; spray-and-pray is what stopped working.

Filter your advice ruthlessly. Only take advice from people who are where you want to be or who you admire. Ignore the rest, including the people telling you that you are burning out.

Frameworks worth stealing

Climb by bringing value, not planning your path

Rather than plotting your own ascent, ask what you can bring to the organization, because you cannot succeed in a company that is not succeeding. Margaret rose from support to CEO by repeatedly proving she could do the next thing the company needed, learning the product and staying close to customers at every step.

Hire on deliverables

Before hiring, answer clearly what KPIs and deliverables the person should own, and lead the decision with that rather than with whether you like them. It prevents homogeneous teams and protects a strong hire from being burned by expectations that were never defined.

Shape the market by what you refuse to build

A product is defined as much by what you decline as by what you ship. Resist the two-month fads even when they are fashionable, because chasing every gimmick dilutes the product, and saying no is a core part of building something durable.

The advice filter

Treat advice as something you actively let in, not passively absorb. If the person giving it is not in the position you want or is not someone you admire, discard it. This applies to strangers and well-meaning peers alike, including anyone insisting you are ruining your career.

Quotes worth keeping

The lines I wrote down.

The role doesn't validate the skillset. Being CEO is a side effect of the story, not the gist of it.

Every channel is dead if you don't know how to use it.

Don't take advice from anyone. Select very carefully whose advice you allow in.

And her take on the passion myth, which the show keeps hearing.

Motivation is a big emotional bump you have today and not tomorrow. Routine and discipline build success.

Rapid fire round

Same questions every guest. No prep, no warning. Here is how Margaret handled it.

Best advice you've ever received? Go through your training even when you don't want to, because you'll thank yourself later.

Advice you ignored or wish you had listened to? That engaging too much in one company is a waste of time because you could earn more elsewhere. She ignored it, and it worked out.

What would you tell your younger self? Focus less on what people think of you, because you don't think about those people daily, so it is a waste of time. She trains the habit like doing push-ups.

Ongoing challenge that keeps you up at night? Catching the market and understanding the next switch, since AI makes everything move faster than ever. She frames it as an exciting part of the job.

Favorite spot? A modern Polish restaurant in Wrocław, for the pierogi or the fish.

Tool you can't live without? Clay for the industry at large, and Bouncer for email validation, which she rates highly.

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Margaret Sikora is the CEO of Woodpecker, a B2B cold email and LinkedIn outreach platform, which she joined in 2017 as a junior customer success specialist and rose to lead in eight years. She also holds a PhD in law. Find her on LinkedIn or at woodpecker.co.