# James Aylward

> 3x PE-backed Exit CPO & GM | Led Product at Pluralsight, Teachers Pay Teachers (acq by IXL), and PerkSpot

Founder of Driftline Strategy, where I advise EdTech, Fintech, AI and marketplace companies on product strategy, team design, and platform growth.

I've led product at four fast-scaling, two-sided platforms:

• Teachers Pay Teachers — \#1 U.S. educator marketplace (acq. by IXL)

• Pluralsight — enterprise learning with expert-instructor ecosystem

• Gazelle — recommerce platform (acq. by Outerwall/EcoATM)

• PerkSpot — led product, tech & marketing to scale the platform

I also founded the AI Incubator at Fidelity Labs (Fintech) part of Fidelity Investments, managed business cards globally for Vistaprint, and have guided multiple companies to PE-backed exits.

Things I can advise on:
✔️ Building a two-sided marketplace
✔️ Balancing supply & demand in marketplaces
✔️ Creating incentives that scale ecosystems
✔️ Product-market fit for EdTech & Fintech platforms
✔️ Position for strategic funding or acquisition
✔️ Clarity on your next product move

Who I Work With:
✔️ EdTech, Fintech, AI founders launching platforms
✔️ Marketplace operators scaling product & GTM
✔️Product leaders shaping AI, org design, or team strategy
✔️Investors & execs prepping for funding or sale
✔️Teacherpreneurs - looking to build a Teacher content store
✔️Australian firms looking to enter the US Market and vice versa

Excited to connect!

## Offerings

- Video call (15 min): $125.00

## Example Questions

- I’m thinking of starting a company. What are the next few things I should focus on?
- How do I know if my business idea will work?
- How would you approach growth for my business?
- What key metrics should I aim for at different stages to be a best in class company?

## Links

- [Expert profile](/jamesaylward)
- [Avatar](https://media.intro.co/avatars/1163356aNaco2ij.jpg)
- [Marketplace](/marketplace)