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Eric Ryan

Co-founder and CTO at Freeplay

Eric Ryan is an experienced software development leader with over 15 years of industry experience.1 He served as the VP of Engineering at MainStreet from December 2020 to May 2022, a tenure of approximately 1 year and 6 months.1

Career Highlights

Current Position: Eric Ryan is currently the Cofounder and CTO of Freeplay, a position he has held since October 2022.1 Freeplay is an AI company, as indicated by his Twitter bio (@freeplay_ai).2

Previous Roles: Before his current role, Eric's career progression included several notable positions:

  1. VP of Engineering at MainStreet (Dec 2020 - May 2022)
  2. Senior Director of Engineering at Twitter (May 2019 - Feb 2020)
  3. Director of Engineering at Twitter (Dec 2016 - May 2019)
  4. Various engineering roles at Twitter and Gnip (2010 - 2016)

Achievements at Twitter

During his time at Twitter, Eric led the Developer Platform Engineering team and managed the Boulder office. His accomplishments include:

  • Overseeing Twitter's Developer platform, including a $350 million ARR SaaS Data Licensing business
  • Leading the transformation of the Developer Platform from a high-touch enterprise business to a hybrid high/self-serve business
  • Consistently achieving the highest retention numbers, offer-to-hire ratio, and employee engagement scores across the company1

Education

Eric Ryan holds two Bachelor of Science degrees from West Virginia University:

  1. Biometric Systems Engineering
  2. Computer Engineering1

Eric is based in Boulder, Colorado, and is known for his expertise in software development leadership and engineering management.12

Highlights

Mar 26 · linkedin

When Ian Cairns and I launched Freeplay, one of our most impactful early decisions was to adopt an opinionated stance on our work culture, specifically how we work. The world, and in turn how we work, has evolved a lot over the past four years. Earlier in my career, I learned the hard way that being overly accommodating and trying to please every working style leads to unnecessary interpersonal conflicts and team inefficiencies. It’s best to lay down the tracks for the team and let people know what they’re self selecting into or intentionally opting out of.

At Freeplay, we've chosen clarity over flexibility. Sharing two of the more impactful operating principles we decided to embrace early on:

🕘 𝐒𝐲𝐧𝐜𝐡𝐫𝐨𝐧𝐨𝐮𝐬 𝐂𝐮𝐥𝐭𝐮𝐫𝐞 & 𝐓𝐢𝐠𝐡𝐭 𝐅𝐞𝐞𝐝𝐛𝐚𝐜𝐤 𝐋𝐨𝐨𝐩𝐬: We have a core onsite presence in downtown Boulder and multiple remote team members spread across three US time zones. We chose synchronous communication, accepting interruptions for the sake of faster decision-making. This approach has enabled tight feedback loops across the team, accelerating our pace. While this can disrupt an individual's flow, the benefit of quicker decisions is what we’ve chosen to optimize for. The team operates around shared core hours and the expectation is that they can close their laptop at the end of the work day and fully disconnect to find balance. I'll note, this is not an indictment of async cultures. There are plenty of successful async-first companies. The key is to commit to one approach and clearly communicate expectations to align the team.

📝 𝐅𝐨𝐜𝐮𝐬𝐞𝐝 𝐒𝐩𝐫𝐢𝐧𝐭𝐬 𝐚𝐧𝐝 𝐏𝐥𝐚𝐧𝐧𝐢𝐧𝐠 𝐇𝐨𝐫𝐢𝐳𝐨𝐧𝐬: Our rhythm involves weekly sprints and six-week planning cycles, also known as “horizons”. We use work-in-progress limits to maintain focus on tasks with the highest ROI for our customers. Each week, we set demoable goals that culminate in a team-wide demo session, where we celebrate our progress together. At the end of each six-week horizon, the team gathers on site in Boulder for reflection, iteration, planning. This in-person time is crucial for aligning our work with key customer needs for the next horizon.

Adopting a clear, opinionated culture has attracted team members who resonate with our values and are enthusiastic about how we work.

I'm curious to know: What working agreements or operating principles have worked well for your team in this new era?

Oct 4 · linkedin

We're growing the team here at Freeplay. We're looking for an AI Engineer and a Full Stack Engineer to join our team.

We're an early stage startup based in Boulder, CO focused on building the platform for product development teams to create & continuously improve production software powered by LLMs! 🤖 You can find out more about what we're up to on our blog (https://freeplay.ai/blog).

Tech: Work with cutting edge AI like GPT-4, Anthropic, Llama2 💻 Runway: Large pre-seed round backed by top-tier investors 📈 Influence: As an early hire you'll help shape the product and culture 👷‍♀️ Traction: Brand name customers as design partners shaping the product 🚜 Expertise: Join our team of industry veterans who built the Twitter developer platform 💪 Views: Located at the foothills of the Rockies in gorgeous Boulder, CO 🏔️

Learn more and apply below! 👇

Related Questions

What are Eric Ryan's main responsibilities at MainStreet?
How did Eric Ryan's role at Twitter prepare him for his position at MainStreet?
What is the mission of Freeplay, and how does it relate to Eric Ryan's career?
What were the key achievements during Eric Ryan's time at Twitter?
How did Eric Ryan contribute to the integration of Gnip into Twitter?
Eric Ryan
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Experience

Cofounder & CTO at Freeplay (Oct 2022 - Present)
VP of Engineering at MainStreet (Dec 2020 - May 2022), Senior Director Of Engineering at Twitter (May 2019 - Feb 2020)

Education

Bachelor of Science in Computer Engineering and Biometric Systems Engineering from West Virginia University (2003 - 2008)

Location

Boulder, Colorado, United States