When you join a startup, you inevitably expect change. For some, the high degree and pace of that change can be overwhelming. However, for those that are able to embrace and thrive amidst the chaos, you are presented with the opportunity to be a critical part of the foundation and direction for your company. 

Recently, our team had the opportunity to meet with an early employee who had just about as much change thrown in her direction as you can imagine. On episode seven of Aspiring Ops, we are excited to be joined by Chelsey Krisay, Chief of Staff at Trainual. 

After what began as a team of four employees building a consulting firm for small businesses, a product pivot found Chelsey at the heart of building an all-in-one training and knowledge platform, now known as Trainual. Fast-forward a few years, and Trainual has built one of the most recognizable names for small businesses looking to scale process documentation, onboarding, and training, serving over 5,000 small businesses across 130 countries,

From roles in Sales and Customer Success to Operations and everything else in between, Chelsey shares how her journey at Trainual led to her responsibility working as an extension of the CEO and overseeing the company’s operating framework as the Chief of Staff. 

To hear Chelsey’s story and how she continues to put a structure in place to help Trainual achieve their goals, listen to the full episode below.

🤹‍♀️ 1:54-2:56 I’ve always been a jack of all trades

💥 2:56-4:30 From client to Chief of Staff at Trainual

🔎 4:30-5:33 Interviewing every employee to identify inefficiencies and opportunities 

🗓 5:33-7:20 Trainual: Day 0 

🙇‍♀️ 7:20-9:00 Bringing on specialized employees

❓ 9:00-10:13  What a Chief of Staff does at Trainual

💭 10:13-12:25 Working as an extension of the CEO

🏠 12:25-14:55 It’s about more than just a framework

💯 14:55-16:17 The importance of grading your meetings

🛤 16:17-18:52 Staying on track with OKRs

🤒 18:52-20:13 People should be sick of hearing their goals they hear them so often

🌱 20:13-22:25 Growing alongside a high-growth company

🔊 22:25-23:25 Career advice from Chelsey, “nothing is too big or too small for you to handle” ‍

👥 23:25-25:21 Combatting imposter syndrome

🔭 25:21-28:29 The future of the Chief of Staff role

Our Takeaway

Trial and error. In our conversation with Chelsey, one area that continued to shine through was the willingness she and the Trainual team had to try something new and iterate as needed. One area specifically was Trainual’s continued investment in finding the right operating cadence and framework for their team. 

For any strategy and operations leader, you are constantly trying to find the right balance for your company as you scale. Nimbleness vs Process. Investing in Product vs Go-to-Market Hires. The list goes on and on. So to help evaluate and surface conversations around these key decisions, you look to implement an operating framework to help surface the necessary information and establish a regular cadence for discussion. 

However, too often we try to build the perfect operating framework right out of the gates with the hope that it will stand the test of time. The reality is your framework should be revisited often. It should be built to evolve with the company. 

The Chief of Staff is the connective tissue between leadership and employees, so it is critical that you are building a framework that evolves to meet the needs of all stakeholders as you continue to scale. 

Chelsey, thank you for taking the time to share how you’ve continued to build a framework that has scaled your team from four employees to 60. We’re looking forward to watching as Trainual continues to grow and provide a leading solution for small businesses everywhere! 

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Interested in learning more about what Trainual? Check out their site here. 

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