$200K - 400K a year
Lead fractional sales executive roles across multiple companies, developing and executing sales strategies and coaching sales teams to achieve goals.
Minimum 10 years as VP of Sales or CSO with proven success in sales strategy, managing and coaching sales teams, ideally across multiple industries.
Is your love for leading a company based on the market dynamics coming into conflict with the realization that you are tired of working full time for one company? Would you love the idea of hands on working as part of the management team of 2 or 3 companies at once, supported by 125 other world class fractional executives? If you have held the position of VP of Sales or CSO at one or more Operating Companies for 10 or more years, but don’t want to go back and do it again, you may be a fit for what we do. Chief Outsiders, www.ChiefOutsiders.com, is a national company that is growing very quickly and is looking to add CSOs in multiple US markets. What We Do: Our focus is on helping midsize companies with the leadership they need for major initiatives in strategy, marketing, and sales management to drive top-line growth long after we are gone. We are specifically looking for qualified sales executives who would love the opportunity to work for two or three companies at once. What We Look For: We want sales executives who can help a CEO or business owner understand where and how to grow and then apply the tools needed to take sales to the next level. If you have a minimum of 10 years’ experience in multiple VP of Sales roles reporting to the CEO then please apply. What It Takes To Succeed: Inquisitiveness, resilience, and knowledge. With no canned approach, we match our fractional executives to the client and they determine how to address the situation. To succeed, you must help the CEO and leadership team understand the real issues and develop and implement a plan that fits the company, opportunity, and competitive situation. Compensation: This is not an “eat what you kill” environment, but we use a revenue share compensation model. You are paid a percentage of the billings for the projects that you work on. You get a bigger share of the revenue if you bring in the lead, but there are company funded programs to help you bring in leads. Most of our CMOs target taking home over $200,000 a year, with some making double that amount. To Be Considered, You Must Have Proven Success • Developing and executing sales strategies • Managing sales teams, both hunters and farmers of 10+ years • Coaching sales teams that consistently achieve goals We seek CSO’s from a variety of industries and business segments. Ideally, candidates have worked in several industries, both B2B and B2C, for large and small companies. • CSOs who love to use their sales leadership expertise to make big things happen, enjoy a variety of challenges, and quickly grasp how to find solutions. • People who love to learn from every assignment and others in the Chief Outsiders Tribe.
This job posting was last updated on 9/12/2025