The journey from individual contributor to VP of Product at Descript wasn't about formal promotions. Instead, it was a gradual process of adding so much value in product discussions that she was invited into progressively more strategic meetings. When you're consistently indispensable in "the room," you eventually belong there permanently.

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Rachel Andrews's journey from planning Cvent's holiday party to Global Head of Events shows that growth comes from executing every small opportunity flawlessly. This hunger to "do more" demonstrates capability and opens doors to greater responsibility, rather than waiting for big, impressive projects to fall in your lap.

To move from engineering to product, don't just ask for the role. Proactively demonstrate PM skills by systemizing learnings from customer interactions. Starting an internal 'customer insight newsletter' based on your debugging work proves your value and builds an undeniable case for the transition.

A zigzag career path across diverse but adjacent roles (e.g., sales, operations, project management) provides a broader, more holistic business awareness. This cross-functional experience is more valuable for senior strategic roles than a narrow, linear progression up a single ladder.

Countering the job-hopping narrative, Rachel Andrews explains her 15 years at Cvent felt like different jobs. Because the team, company, and goals constantly evolved, she continuously expanded her role without leaving, proving that long-term commitment at a dynamic company can be a powerful vehicle for diverse professional growth.

Don't wait for a promotion or new job opening to grow. Proactively identify other teams' pain points and offer your expertise to help solve them. This proactive helpfulness builds relationships, demonstrates your value across the organization, and organically opens doors to new skills and responsibilities.

A linear career path is not required for success. Businesses ultimately value high performers who demonstrate an ownership mentality and consistently drive impact. Focusing on helping the business win creates opportunities to move across roles and industries, making your journey more valuable.

The pivot from a pure technology role (like CTO) to product leadership is driven by a passion shift. It's moving from being obsessed with technical optimization (e.g., reducing server costs) to being obsessed with customer problems. The reward becomes seeing a customer's delight in a solved problem, which fuels a desire to focus entirely on that part of the business.

When transitioning into a new role, especially a cross-functional one like product, relying on a title is a weak foundation for credibility. Earning respect through informal authority—by demonstrating value and influence—builds a much stronger and more lasting leadership position.

Startup Career Progression Isn't a Ladder; It's Being Invited Into More Important Rooms | RiffOn