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For people breaking in and leveling up in tech sales. Live coaching from a pro who's changed lives, crushed quota, and made millions, plus a full curriculum and a 24/7 AI practice partner.
AWS · Google · Dell · Shopify · Insight · Confluent · Check Point · Arctic Wolf · Geotab · Optiv · SADA · Softchoice · Pythian · Higher Logic · Socket · Broadwing · iSmile Technologies · Tracktile · PayerPrice · Revelate · Vocantas · Vaital · Next Orbit · Beverly Hills Publishing · Appsonnet
This includes official and unofficial mentoring. Not an endorsement, partnership, or guarantee of employment. TSRE is a coaching program, not a placement service.
Tech sales pays well, moves fast, and won't ever be less important.
Help companies find and buy software. Calls, emails, and online meetings. No knocking on doors, no products in a trunk.
Remote or hybrid, from anywhere. All you need is a laptop and a headset.
Base salary plus commission. The more you help close, the more you earn. Top reps earn well into six figures.
No degree, no coding. People from retail, hospitality, teaching, and sports. Drive and coachability win.
No salary band decides your ceiling. The better you get, the more you make. I built my whole life on that simple deal, and I'll hand you the playbook.
Software gets bought by people who trust people. Tools speed up the busywork, but the trust and the close are still yours. That's the part I'll teach you.
I've watched people with no degree out-earn lawyers and engineers. This career pays you on skill and drive, not pedigree. If you'll do the work, you're welcome here.
Learn to sell once and it pays you forever. The skill travels with you to any company, any product, any market. Nobody can take it back.
Learn it, build it, practice it until it's second nature, then master the six skills that make up the job.
Self-paced video modules covering every stage of the B2B tech sales motion. Two recommended paths: one for Breaking In, one for Leveling Up. Same library, different routes through it.
Twice-weekly group sessions for 10 weeks. Practice, role-play, real deal reviews. Reinforce what you've learned in the library and build the skill until it's reflex.
A proprietary AI trained on the TSRE methodology. Role-play cold calls, discovery questions, objection handling, demos. 24/7 access. Instant feedback. Practice until reflexes are sharp.
Find the right people and get them to reply. Emails that get opened, and calls that book meetings instead of hang-ups.
Ask the questions that surface what someone actually needs, so you know exactly how to help.
Show the product so the value is obvious, and make saying yes to the next step easy.
Answer "too expensive," "not right now," and "we already use someone" with calm, practiced responses.
Turn interest into a signed deal with a clear, repeatable process. No begging, no luck.
Stay on top of every deal so nothing slips and you always know what is coming.
Build a sales resume that lands interviews, even with zero sales experience. We position what you already have so it reads like a hire.
Mock interviews with me and the AI partner. Drill the questions, the role-plays, and the close, so you walk in calm and leave with the offer.
Turn your profile into something hiring managers and recruiters actually reach out to, instead of scrolling past.
Skip the application black hole. Message the people who actually decide, the same way top reps prospect their best accounts.
I tailor the program and the investment to where you're at and where you're headed. Apply and we'll talk it through.
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I've spent 22 years in B2B tech sales, closing over $114M and helping build companies from startup to scale. I grew SADA's Canadian team from 2 people to 200+ in under 3 years, and have trained, mentored, and promoted more than 100 reps.
Some run sales teams now. Some hit President's Club in their first year. All of them learned the method I teach.
One rep started with zero tech sales background. Three years later, he was running an entire country as country manager.
I've sold tech for two decades and trained people who now out-earn their old jobs. Not a coach who watched from the sidelines.
I've coached reps through every stage of a tech sales career. The patterns repeat. The practice works.
I don't gatekeep on pedigree or résumé. Anyone willing to work is welcome. Put in the reps and I bring my network to you. That's how people go from breaking in to leading teams.
Ben inspired me to pursue a career in tech sales, leaving behind a job I considered safe and stable. His influence helped me develop the drive that led to 3xing my income. Highly recommend working with him!
What I loved about Ben was his ability to develop and he was a top sales rep who always took my call to make sure I was developing right. I'd recommend Ben: creative in his processes to succeed, inspiring others to win, and always willing to teach.
Ben is a force of nature. His ability to manage the complexities of being a great mentor and source of inspiration and knowledge to a flock of mentees (myself included) is incredible.
It was a pleasure to work with Ben at such a pivotal point in my career. Always leading by example, inspiring and motivating many, myself included. His hands-on approach to career coaching and his enthusiasm for the work are contagious.
Ben was instrumental in helping me go from struggling to understand why my deals weren't closing, to qualifying leads in the first meeting and having a much clearer picture of where each deal stood in my pipeline. On top of that, my ability to close has improved significantly!
Ben leads with value first! He has been the biggest support, willing to go above and beyond and take the time to help me when I'm stuck or have questions. A wonderful experience, and I look forward to continuing to learn his insights. He is excellent at what he does!
I was eager to mature my sales career and Ben was a key mentor: encouraging, sharing keen insights, and pressing me to reach beyond my current role. He played a huge role in taking my career to new heights. I'd strongly recommend Ben.
Working with Ben, I've booked more first-time appointments than I ever have before, from his cold calling coaching and sales mentoring. Highly recommend working with him!
Ben's sales knowledge and candid feedback were very much appreciated. He helped me onboard my new AE team well ahead of schedule with great sales methodology training, coaching, and documentation. Much appreciated.
I wasn't in tech sales before working with Ben. His tips and tools kept me motivated, and the interview practice we did before I got hired made me completely comfortable and it felt just like a conversation. Now I'm in, and I can make six figures in my mid-20s. So grateful!
I came from the government into tech sales and Ben taught me everything I needed to become a rep. He pushed me to take the leap and nine years later, I'm still going strong. You da man, Ben!
Ben has an unwavering drive to make those around him better. He hired me from outside of tech sales in 2021 and I've never looked back, rising to SADA Canada Country Manager in under 4 years. There are few people who have had as much impact on my career as Ben. A strong leader, and an overall good guy.
These are individual results and not a guarantee of yours.
Two audiences. Breaking In is for career-changers, recent grads, and people in adjacent roles wanting their first B2B tech sales job. Leveling Up is for current SDRs, AEs, and senior AEs pushing for the next promotion, comp jump, or President's Club. Same cohort, same live sessions, different recommended paths through the curriculum library.
Ten weeks. Two live coaching sessions per week (roughly 2 hours each). Self-paced video curriculum on top, consume at your pace. AI practice partner available 24/7. Plan on 5-8 hours per week to get the full value out of the program.
No, and you should be suspicious of any program that does. What I guarantee is the system, the live coaching, and an AI partner to practice with until the skills are reflex. Outcomes are a function of your effort plus the framework. The reps who do the work get hired or promoted.
You'll follow the Breaking In recommended path. It starts with B2B tech 101 (how SaaS works, what ARR is, the tech sales career ladder) before getting into the craft. By the end you'll have the foundation and the reps to walk into interviews and land your first SDR role on merit.
No. The Leveling Up path covers full-cycle selling, winning bigger multi-stakeholder deals, accurate forecasting, negotiation, discounting discipline, and career strategy (offer evaluation, comp negotiation, when to move). Most AEs are running half a system. TSRE closes the gaps.
Lifetime access to the curriculum library, the AI practice partner, and the alumni community. Once you're in, you're in. The skills compound for the rest of your career.
No. Anyone willing to work is welcome. Pedigree and résumé don't decide it. Everyone trains on the same system. Put in the reps and rise, and I open my network to you. The bar isn't who you are walking in; it's how hard you push once you're here.
Most tech sales programs are taught by reps who broke in two or three years ago. That's a peer with a head start, not a teacher. I'm a 22-year sales veteran who closed $114M and grew SADA Canada from 2 to 200+ people. The depth of experience shows up in every session.
Application required. I review every one and reply within 48 hours.
Not ready to apply? Join the free Skool community →