Confidence, Conviction, and the Courage to Lead: Breaking the Mold to Become CEO
- Rashmi Vittal
- Aug 18
- 5 min read
This article is Part 2 of the full blog series 'Breaking Through: GTM to CEO" by author and friend of Wednesday Women, Rashmi Vittal.
Christine Heckart doesn’t believe in trying to be ‘better’ – she believes in the value of being different. Distinct. Unique. That simple shift in mindset has been core to her leadership journey, one that spans CMO and GM roles at major tech companies like Microsoft, Cisco, and Juniper, and includes CEO roles at Scalyr and now Xapa, the company she founded.
We spoke about what it really takes to break through to the CEO seat—especially for leaders coming from go-to-market (GTM) backgrounds—and the themes were loud and clear: confidence, conviction, and the courage to be different.
"If it were my decision, I'd do it differently."
Christine knew early in her career that she wanted to be in charge. She started as a product manager, launching new products that were ‘first’ in their category, and was always focused on driving broader business outcomes. She developed a strong point of view on the business and wasn’t shy about sharing her point of view with her CEO and peers – take it or leave it, she wanted them to at least consider it. And she has a reputation for thinking big and being unconventional. It’s not always comfortable for people, but it’s usually provocative.
“I would always challenge myself by thinking, ‘If it was my decision, I would do this and not that.’ ‘I would take this risk or make that bet.’ I had conviction in how I’d lead.”
Unlike many women I’ve interviewed who didn’t explicitly seek out the CEO role, Christine was intentional. She had always wanted to be a CEO and while working at Cisco, she openly shared with her team that becoming a CEO was what she wanted to do ‘next’. Those who worked with her knew this wasn’t just a passing interest—it was a goal. That clarity led to her first CEO opportunity.
Not the Expected Choice – But the Right One
A CEO recruiter reached out to one of her direct reports, who recommended her: “My boss wants to be a CEO, and I think she would make a great candidate.” That led to an opportunity, but Christine wasn’t the early favorite. The board already had a candidate who was further along in the process and perhaps a bit more aligned—at least on paper—with the desired requirements. Christine was the only woman under consideration and didn’t come from that specific domain. At the time, it was rare for GTM leaders to be seriously considered for CEO roles—especially in highly technical companies. As Christine put it,
“They took a chance on me. I’ll be forever grateful to the recruiter (Pete Steinle), the Founder and CEO (Steve Newman), and the lead investor (Jason Pressman).”
She doesn’t know exactly why, but knowing Christine, I’d guess it was a combination of her extensive GTM experience, her leadership philosophy—and maybe the originality with which she articulated it all. It clearly made an impression.
Leading with Style (and a Farside Cartoon)
In her final interview, Christine was asked to present her strategic vision for the company. She took a different approach. She told me:
“I didn’t know the technology or the market well enough to have a fully formed strategic vision, and I believe in starting with first principles. I want to understand the context, not assume I can use a previous playbook.”
Therefore, her presentation to the decision-makers focused on questions, not answers, and HOW she would lead: her values, her decision-making style, how she operates in uncertainty. She used Farside cartoons to illustrate her points. And in doing so, she embodied the very philosophy she was there to pitch—be different, not just better.
Confidence Opens Doors—Networks Keep Them Open
Christine is quick to credit the people who bet on her along the way—mentors, colleagues, former bosses, even customers. But the common thread across all those opportunities? Her extensive network. Someone in her network who was willing to bet on her. She emphasizes the importance of nurturing those connections with a “give before you get” mindset. She believes deeply in helping people, using her platform to pull people up, and not expecting anything in return. Whether its people just coming into the workforce, seeking their first promotion, C-suite role or board role.
But more than anything, Christine believes what moves the needle isn’t perfect qualifications—it’s clarity, courage and conviction.
“I don’t pretend to know all the answers. But I’m clear about how to be curious and go find them.”
A Message to GTM Leaders: Stop Trying to Fit the Mold
One of the biggest challenges GTM leaders face on the path to CEO is the misperception that they’re too commercially biased, too light on technical depth, or not strategic enough. Christine flips that narrative.
“Why is it acceptable for a technical founder to lead a go-to-market team without ever selling or marketing anything—but not the other way around?”
The reality is, Christine is very technical, especially for a GTM leader. But her point is that adaptability, creativity, problem-solving, and other skills are what’s most important in leadership. Leadership – being a CEO – is about listening, adaptability, and the soft skills, not just what’s on the résumé.
And the reality is, Christine had been a business builder and leader early in her career. At TeleChoice, she was hired to start a new division around ‘data and technology’ and built it from scratch. She led the P&L, ran all functions, and turned a one-woman team into a global growth engine that ultimately propelled the company forward for years. That experience cemented her ability to lead at the highest level.
Own the Room by Owning Yourself
For women especially, the path to the CEO seat can feel narrow and coded. Christine’s advice is refreshingly direct: Don’t try to be the best version of someone else. Be the most clear, courageous and compelling version of you.
Her story reminds me that the real breakthrough begins when you know your value—and believe in it.
The author, Rashmi Vittal, is a GTM Executive and Advisor with 20+ years in enterprise software scaling B2B SaaS and AI companies between $10M to $100M ARR. She’s led marketing and GTM Strategy at high-growth startups, turnarounds and public companies like IBM, Oracle, and SAP—shaping categories in disruptive markets; e.g. Content Analytics, Conversational AI in RevTech, digital identity, and data and analytics. She is ready to be a CEO of a growth-stage AI company, partnering with the right investors and founders to scale efficiently and build long-term enterprise value.
