From burnout to breakthrough. How this former founder landed her dream job at a top venture capital firm

Anisha Gupta x Katy Culver

Anisha successfully exited her startup and took a career break to recover from burnout. After rebuilding her life, she was ready to re-enter the job market. But she didn’t want another job at the cost of the life she’d built. 
 

In just four months, she went from being unclear on her career goals to landing a dream role at First Round Capital, a top VC firm. 

This is how she did it.

The Challenge: Is this right? 

Anisha Gupta spent the last eight years of her career leading operations across companies in tech and CPG, both as a founder herself and as a trusted advisor for others. 

As a true generalist, she’s done everything under the sun in strategy and operations: a create-order-from-chaos expert!

After decompressing and building the life that she wanted, she faced the uncertainty that many do after a professional break: How do you transition back into meaningful work when you refuse to sacrifice the life you've fought so hard to create?

Deciding on your next career move as a generalist can be challenging – especially after being a founder who’s done it all.

For Anisha, it was a matter of creating a good balance between what she wanted to pursue and honoring the new priorities in her life.

The Shift

After joining The Purposeful Path Accelerator (PPA), she learned to leverage her unique value as a startup pro to define her goals and land her next role. 

Inside our community, Anisha shifted her approach to the job search. She became a Stand Out Candidate: the top 1% candidate that hiring teams can't afford to pass up.

She leveled up her cold outreach game, got more strategic about leveraging her already supportive network, and started intentional conversations.

She became a strategic player in the job search market.

She became THE candidate to talk to.

All while honoring her boundaries.

Here’s when having a support system is key.

As a generalist, you know what you bring to the table, but putting yourself out there sometimes may be a difficult journey. 

Anisha found a strong community inside PPA with people just like her: driven to do meaningful work and support one another. 

"Lean into community when you need support, and people will show up for you.”

Where is Anisha now?

Two months into her five-month contract, Anisha got a full-time dream role offer from First Round Capital doing founder support and go-to-market strategy.

She’s now helping other founders navigate the exact challenges she'd mastered herself.

Anisha landed a job that values her past experience, challenges her to grow, and aligns with the boundaries she worked hard to define.

Thank you, Anisha, for sharing your journey!

As she put it: “As a generalist, you literally can't go wrong joining this program”.