< Back to All Insights and Resources

6 Strategies an Entrepreneurial Boston Firm Used to Achieve Massive Growth and a Huge Exit

6 Strategies an Entrepreneurial Boston Firm Used to Achieve Massive Growth and a Huge Exit

Don Schiavone: We want people to fail quickly, learn, and move on.

Guest:Don Schiavone

Bio in a Tweet:COO of Grasshopper, company just sold to Citrix, 20-year track record of helping businesses of all sizes scale their operational processes, Wharton grad, triathlete.

Quick Background:Grasshopper is a fast-growing virtual phone service for entrepreneurs. The company was just sold for a substantial amount of money. In today’s show, we explore the 6 strategies that led to Grasshopper’s rapid growth and how you can apply these strategies in your business, too.

Grasshopper’s 6 High-Growth Strategies

Actively nurture a high-growth culture. To refine the culture, the leadership asked employees, “What do you think our culture is?” Next, the leaders asked employees to, “Give us a story that demonstrates someone in the company living that culture.” From there, they developed four cultural values that correlated to a high-growth successful company.

Get the right people on the bus. And not only that, Don said, “Having the right team at the right time of each stage of growth is critical.” For example, the person leading the initial high-growth phase of the company may not be the person to lead the mature growth phase.

Give the team a purpose then get out of the way. Don said, “The purpose isn’t let’s make money, let’s go public.” Rather, “It’s got to be something that’s much more tangible, something that can really empower your team to get behind and do great things.”

Create incentives that align with the company’s purpose and reinforces its culture. For example, Grasshopper is “policy light.” They see that as an incentive for employees, such as phantom stock options, because it allows them to work differently, think differently, and be treated as smart adults who don’t need detailed company policies to follow.

Relentlessly measure and test everything. As Mark Moses says, “If you can’t define it, you can’t measure it. If you can’t measure it, you can’t manage it.” Don and his team are constantly “firing bullets” to see what works before moving full-steam ahead.

Hire a business coach who’s been there, done that. Don said, “To have someone that learns your business but has an outside perspective that you can bounce ideas off of, can challenge your thinking before you go and act, is invaluable.”

Coaching Takeaways:

About Don Schiavone

Don brings over 25 years of experience leading high-growth businesses. He brings together an in-depth understanding of technology with a data-driven “test-everything” philosophy: You can’t manage what you can’t measure. Don’s approach to coaching focuses on three pillars of success: people, process, and systems, in that order.
Learn more

About CEO Coaching International

CEO Coaching International works with CEOs and their leadership teams to achieve extraordinary results quarter after quarter, year after year. Known globally for its success in coaching growth-focused entrepreneurs to meaningful exits, CEO Coaching International has coached more than 1,000 CEOs and entrepreneurs in more than 60 countries and 45 industries. The coaches at CEO Coaching International are former CEOs, presidents, or executives who have made BIG happen. The firm’s coaches have led double-digit sales and profit growth in businesses ranging in size from startups to over $10 billion, and many are founders that have led their companies through successful eight, nine, and ten-figure exits. Companies working with CEO Coaching International for two years or more have experienced an average EBITDA CAGR of 67.8% during their time as a client, nearly four times the U.S. average and a revenue CAGR of 25.5%, more than twice the U.S. average.

Learn more about executive coaching | Meet our world-class coaches

Related Content

05.23.2022

2022 Make BIG Happen Summit on Oct. 20-22 in Mi...

CEO Coaching International Announces 2022 Make BIG Happen Summit on Oct. 20-22 in Miami Beach The Firm’s Annual ...

Read more
asset protection
05.18.2022

Why All CEOs Need an Asset Protection Plan

Guest: Hillel L. Presser, Esq., Managing Partner of The Presser Law Firm, P.A. Overview: CEOs who lead a company to B...

Read more
Altis
05.16.2022

CEO Coaching International Congratulates Client...

CEO Coaching International Congratulates Client Altis on Closing $10.5M Seed Round MIAMI, Fla., May 16, 2022 — CEO...

Read more