I’m Lester Sydney, a relationship-driven sales expert with over 17 years of proven success, dedicated to empowering startups and leaders to achieve their dreams.
My journey began with a clothing design that sold out at Urban Outfitters in just 2 weeks, leading to sales with top online retailers, a venture I later closed after four years of breaking even. That early experience taught me the power of relationships, a lesson I’ve carried through every role since, from tripling sales from $1.5M to $4.5M as CEO of Maine Flower Holding Corp, to securing major deals with clients like Equifax, Citi Bank, and ADP during my time at Synopsys and Black Duck Software, where I was named the #1 Sales Rep globally and a frequent President's Club member.
Today, as a Head of Sales of Northeast & Southeast at Percona, I help companies optimize database performance. Beyond my work, I’m passionate about giving back, serving as a Sales Mentor at Harvard Business School, an Advisor to the Board at Elevated Thought, and holding advisory positions at CGM Sports and AccountAim. With a career rooted in building trust and driving results, I’m here to spark your mind and fuel your dream. Let’s connect to turn your vision into reality.
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Since working with Lester, we’ve seen a significant improvement in sales results! He unlocked a whole new perspective for me. Not just on how to approach sales, but on improving communication and making meaningful conversation with prospects and customers.
Lester has been an incredible mentor and asset for us at CGM Sports as he continually pushes us to be the best version of ourselves. Lester has been selfless and is willing to help us work through our company's most difficult problems. He is always willing to go the extra mile for us and has helped me progress as an entrepreneur and leader.
Lester’s coaching has had an immediate positive impact on me and has enabled me to take ownership in my career. I appreciate his direct communication style, high level of professionalism, and his years of tried-and-true experience he brings to the table. I am continuously improving personally and professionally under his mentorship.
There are 3 words to describe the impact of Lester's mentorship: valuable, authentic, and life-changing. Through learning from his experiences and expertise, I've truly become a better overall human being.
Lester has been instrumental in advising AccountAim’s GTM efforts. He has the unique ability to dive deep into tactical sales coaching while also understanding the bigger picture of launching a startup. He has had a hugely positive impact on our traction as a business.
Lester has been instrumental in shaping our startup's strategy and growth plans. His guidance in our negotiations with a high-profile athlete was invaluable, and his willingness to assist in all areas of our business has been exceptional. Lester's expertise and dedication have truly been a cornerstone of our success.
Working with Lester was critical to my transition into B2B sales. He helped me develop a framework that I have used to thrive in my role as an Account Executive. That success helped me get promoted into sales leadership, and now train a team of people in a similar fashion.
Lester is an extremely empathetic and self reflective individual who finds genuine joy in helping others and contributing to their success. In just one year, I learned more about sales from Lester than I did in the past several years of my professional career. Lester is more than just my sales mentor, he’s a great friend 💪
Embark on a transformative journey with our Start-up GTM & Sales consulting services.
Too often, startup sales are steered by founders and CEOs who lack prior sales experience or haven't led a sales cycle before. Through my extensive involvement in advisory boards, guiding startup founders and CEOs in their Sales and GTM strategies, I've witnessed recurring challenges that can be swiftly resolved with the expertise of a seasoned sales professional.
Here are the common hurdles I frequently encounter:
Let me guide you through these obstacles and unlock the full potential of your startup's sales journey.
If you're grappling with any of the challenges mentioned above, don't hesitate.
Reserve your FREE 30-minute consultation now to explore how I can also assist you and your team.
WHAT YOU GET:
12-month Start-up GTM & Sales Consulting
With 16 years of experience in sales, I've weathered the highs and lows of this dynamic field. Through my journey, I've come to understand that sales is primarily a mindset game. Those who adeptly navigate the lows emerge victorious, while those who struggle may find themselves stagnant.
Are you currently facing a slump in your sales career or feeling far from where you aspire to be?
Rest assured, I've walked that path too. Drawing from my own experiences, I've cultivated the essential mindset tools needed to propel my growth and excel in sales.
WHAT YOU GET:
12-month Sales Mindset Coaching
Secure your FREE 30-minute consultation now to determine if I am the ideal coach for you.
