Call Me 978-231-3890

Stephen Osterman

Founder & Outsourced VP of Sales

Serving Greater Boston, MA

I Can Help Provide You a Path to Consistent Sales Growth

As an Outsourced/Fractional VP of Sales I can deliver the process and results you expect. If you are ready to take the first step in creating a solid sales foundation, call or email me to schedule a FREE SALES CONSULTATION.

About Me

I founded The Sales Solutions Group to specialize in delivering the expertise to unlock the keys to sales excellence. I focus on sales strategy, process, and execution aligned to meet your needs. The results are revenue growth and sales acceleration.

With my 25+ years of sales leadership working with Fortune 500 brands, from top sales executive to leading high performance regional and national sales, customer success, and business development teams, I bring the passion, know-how, and inspiration critical to transforming your sales organization.

I do this powered by the industry leading sales platform from Sales Xceleration.

I Do The Work For You

My goal is to drive sales growth. I do this with Sales Xceleration’s proven system that focuses on creating record-breaking sales for your company, defined in these 3 steps:

  • Create a Sales Plan
  • Find Your Best Customers
  • Grow Your Sales
Get Immediate Tips on Turning Your Sales Around
Take FREE Assessment


Over the next few months, I will be engaging in the following activities within my community:
  1. Joining a mentorship program mentoring young adults looking to enter business and technology organizations. I am currently looking at the Hack Diversity Program.
  2. Becoming a member of our local Chamber of Commerce and providing business advice to local business on a pro bono basis.
  3. I have set up a coffee group to build friendship and support for professionals who are thinking about or in process of a transition in their lives. We meet locally on Friday mornings to share experiences and advice.


"I had the pleasure of working closely with Steve at Fidelity Investments during the company’s explosive growth years marked by opening multiple regional call centers and expanding sales, business development, and customer success workforces exponentially. Without question, Steve was one of the top leaders in the national organization, during his years managing teams in Dallas, Salt Lake City, and Boston. Amongst the attributes Steve brings to the table are strong leadership skills, deep industry knowledge, poise under pressure, the ability to manage competing priorities, and a work ethic matched only by Steve’s terrific sense of humor. The quality that stands out for me is Steve’s ability to build productive relationships and business partnerships while leading those partnerships toward win-win results for the benefit of customers and the business. Further, working with Steve guarantees high energy, collaboration, and absolute fun while driving business results. Steve is a pleasure to do business with, and I highly recommend Steve as an outstanding leader and business partner. "

- EAG Associates LLC- Business Consultant – Nick Norton

"Steve is a dynamic, well-rounded businessperson. He offers a unique perspective and approach to both sales and strategy. Beyond solution selling, Steve gets both the company he represents and the client/prospect he is focused on, to visualize a future state that achieves both parties’ goals. He then has the ability, and personal drive, to coordinate process, people and technology to achieve the win/win future state. During my years managing Steve, he was one of the top salespeople in the country. However, his contributions to strategy and corporate growth went well beyond his direct sales efforts. Steve led us toward adopting new technology, expanding into new market opportunities, redefining selling approaches and embracing new value propositions. His efforts helped catalyze a dramatic divisional turnaround. If you are servicing the financial services industry, and looking for a transformational growth leader, I would strongly recommend you take a moment to meet Steve Osterman."

- Managing Partner SellingCX – Ian Levine

"I have known Steve Osterman for twenty-five years. Steve led the channel partner selling of our sales enablement Storefront Technology enterprise software. Steve's sales leadership, communication and solution selling professionalism enabled our company to grow from start-up status to providing solutions to over seventy (70) Fortune 500 companies across financial and healthcare services. Steve is the ultimate sales professional, providing market insights, strategy, communication and resolving complex issues. Steve has significant leadership professionalism to provide breadth and depth to drive your sales process to success."

- Firm Founder and Principal Celera Systems LLC - Gary Maradik

"Having known Steve for over 30 years working in various capacities, Steve has always shown great leadership, solutions-oriented approach and the highest level of integrity. His no nonsense approach pairs well with his strong communication style and collegial personality. Steve has always achieved what he sets out to do and it has been a pleasure knowing and working with him. If you have a need to work with him, you will see successes and enjoy the process. "

- Board Chair, Independent Trustee – Christopher Wilson

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Face the Future with Confidence

I understand that leading and growing your company is hard work. Many business leaders don't have the time or the energy they need to grow their sales and put a strategy in place that will work for years to come. If you are tired of not having a clear path, it's time to take the next step and partner with a sales leader who has been down the road before and can guide you to sales success. Get started today!