About Simon Stillwell
With a track record of successfully launching foreign businesses in the US and experience across various growth phases, Simon’s expertise is versatile. As an advisor and fractional Chief Sales Officer (CSO), he helps businesses tackle all types of sales challenges from fixing ill focused poorly performing sales people and their managers to how to enter a new territory or market effectively.
The majority of Simon’s experience has been earned in Fintech, specifically with companies selling software and SaaS primarily but he has successfully guided sales organizations in other verticals and completely different industries.
Beyond his professional accomplishments, Simon is a keen sailor with many ocean miles and a transatlantic race under his keel.
Random Facts
Age of first sale
Board Positions
Sales teams built and managed
Transatlantic sailing race completed
Specialization as Revenue Leader
My specialty is in sales strategy and management with broad business experience through board member and executive board roles at multiple public and private companies. I have experience acquiring businesses and being acquired, as well as ramping up for sale and pulling diverse teams together afterward. I have successfully brought multiple foreign businesses to the U.S. from overseas and worked through the myriad challenges, and now I advise companies pursuing this expansion opportunity. I am passionate about helping businesses achieve revenue success through getting the 4 P’s right – People. Product. Process. Price.
Deepest Industry Expertise
High value, long sales cycle, Business to Business (B2B) software and SaaS, primarily in the Fintech space where retention rates and account management are key to driving annual recurring revenue (ARR) growth.
Improve Sales Conversion Rate
- Sales strategy
- Right people in the right place
- Right systems to manage and motivate
- Sales team management
- Compensation, team structure, distribution
- Proven and repeatable sales process
Advise international & domestic expansion
- Ideal Customer Profile (ICP)
- Unique Sales Proposition (USP)
- Gaining a beachhead client
- Growing revenue from overseas
- How and when to put down roots
Greatest Professional Passion
Transitioning un-focused, un-managed or under-managed sales teams to successful, motivated contributors to the company’s accelerated and sustainable growth.
Simon Stillwell
Key Engagement Methods
Fractional Chief Sales Officer (CSO)
Effective sales management is vital for business growth. Teams of 10 or fewer salespeople often do not need a full time sales manager, nor can smaller businesses afford experienced managers. Fractional management is the answer.
International or post acquisition expansion
Getting these right, from a sales point of view is critical to profitable revenue growth and full of potential pitfalls. When navigating these it is good to have someone on the team who has done it before.
90-day Revenue Roadmap
Running a business is like navigating across an ocean, you need to make constant checks and course alterations to ensure you arrive at your destination. We assess your current trajectory and make recommendations as to how to get you back on course.
Podcast: Coming to America — How to build, grow and sustain a business in the US
Bringing their product to the US is the goal of many foreign companies, lured by the vast market it represents. “If we can crack the US market we’ll be made” or similar sentiments have been heard in boardrooms across the globe for decades. Like all great endeavors however, it is not easy and many companies fail or spend fortunes trying.
Listen in to learn some key things to think about if you are considering taking this journey and contact Simon if you would like further advice or if you need help getting back on course.