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This week, the Free Agent Sales Combine brought in Benjamin Roach to talk to our athletes about what it actually takes to succeed in sales, and what's waiting on the other side if you do.
Ben is the Director of Revenue Operations at a Series A SaaS startup. He leads a team of 12 supporting compensation operations tied to nearly $3 billion in assets across hundreds of public companies. Before that, he was an SDR who burned out. Before that, he was a cop. Before that, he was a professional rugby player who fractured his spine three weeks before the Rio Olympics and was told he would never walk again.
He walked. He played. And then he built a career that most athletes have never heard of.
He did not come in with a polished keynote. He gave our athletes the raw, honest playbook that took him years to learn: what RevOps leaders are actually looking at when they evaluate reps, what separates the reps who get promoted from the ones who get cut, and why the career path he landed on might be the best-kept secret in tech.
Here is what he told them.
From Rugby to Revenue Operations: A Path Nobody Would Have Predicted
Ben started playing rugby professionally at 16. He spent a decade competing across Europe and earned a spot with the US Olympic team. Three weeks before Rio, he fractured his L4 and L5 vertebrae. His playing career was over.
He went straight into sales. Was given a phone, a quota, and the standard line every athlete hears: 'You're a pro athlete, you'll be great at sales.' He had no idea what that meant.
"I was an SDR. Everyone told me, 'You're a pro athlete, you're going to make a great salesperson.' I had no clue what that meant. Zero clue. So I was given a phone, I was given a quota, and that was it."
Benjamin Roach, Director of Revenue Operations, Optio Incentives
He burned out. Had what he calls a midlife crisis in his late 20s and became a cop. After three and a half years in law enforcement, his wife told him he was done. He pivoted back into tech, found revenue operations, and built the career he has today.
The path was not straight. That is the point. Ben told the Sales Combine that pivoting is not restarting. Every stop along the way built something. The discipline from sport. The real-time decision making from law enforcement. The sales instinct from the SDR floor. All of it feeds into RevOps.
What Ben Told Our Athletes About Succeeding as a Rep
Ben did not hold back. He gave the Sales Combine the tactical playbook that most reps do not learn until their second or third year on the job. Here is what he told them.
Your CRM is your game tape.
If you played competitive sport, you know game film does not lie. Your coach watched every shift, every play, every decision. Your CRM is the corporate version. Every call you log, every note you write, every deal stage you update. That is the only thing representing you when decisions about your career are being made in rooms you are not in.
"There are decisions being made about you and your career when you are not in the room. Think of your CRM as your game tape. If it's not in there, if they can't see what you're doing, that decision's being made without your opinion."
Benjamin Roach
The data backs it up. Companies with clean CRM data consistently outperform on forecasting accuracy. Ben's analogy: treat your CRM like a tax return. Nobody loves doing it. But if it is not done, nobody believes you.
Know your pipeline math.
If your company needs to close six deals this quarter at a 40% close rate, you need 15 deals in the pipeline. If it takes 40 calls to book one meeting and 48% of booked meetings never show up, you can calculate exactly how much activity you need to hit your number. The average SDR makes about 36 calls and 33 emails per day. Cold calling converts at roughly 2.3%. Most new reps do not think this way. They show up, make calls, and hope. The reps who hit quota reverse-engineer their activity from the math.
Ben told the team: know your own numbers, not the company average. How many calls does it take you to book one meeting? How many of your meetings actually show up? Once you know those numbers, you own the conversation with your manager instead of the other way around.
Watch out for happy ears.
Happy ears is the single most common mistake new reps make. A prospect says something positive and you hear a commitment that was never made. 'Send me a proposal.' 'I love this, let me show my boss.' 'Definitely send me an email with more info.'
"Compliments are the quietest way to end a conversation without telling you no. If your champions are telling you, 'This is amazing, I'm going to show my boss,' but you haven't talked to their boss yet, that's a warning sign."
Benjamin Roach
Athletes actually have an edge here. You have spent your entire career reading body language. You know when a coach is telling you what you want to hear versus what is true. Use that instinct on sales calls. If something feels off, it probably is.
Learn to forecast honestly.
Forecasting is when your manager asks which deals are going to close and you give them a number. Fewer than 25% of sales organizations get within 10% of their actual results. Ben described it as the constant tension between gut and data. A rep says 'I believe in my champion.' RevOps looks at the data and says 'You have not started the legal process and procurement takes three months. This is not closing this quarter.' The reps who forecast conservatively and then beat their number build trust that compounds. The ones who over-promise and miss lose credibility fast.
Never leave a call without booking the next meeting.
This was Ben's most emphatic point. He has years of data on it.
"Don't leave a call until you've booked the next meeting. Reps that actually do that have a 90% show rate and a three to four times higher quota exceeding rate than reps who just wait and don't book that next meeting."
Benjamin Roach
Independent research confirms the pattern. Calls with clear next steps are 2.7 times more likely to lead to a successful outcome. If you are in a 30-minute presentation and realize with 10 minutes left that you are not going to cover everything, stop. Pull up your calendar. Book the next meeting. The content can wait. The momentum cannot.
Do not confuse activity with progress.
Ben hears junior reps say '50 calls this week' or '1,000 emails sent.' His response: what did it produce? Sales reps spend only 28 to 30% of their week on revenue-generating activities. The reps who win are not doing the most work. They are doing the most effective work. Find what produces results for you and double down. If you are great on the phone, make the phone your weapon. Your manager cares about output, not motion.
How to Get From Sales Into RevOps
Master your CRM: Ben said if someone walked into an interview and said they loved working in a CRM, he would hire them on the spot. Nobody says that. The athletes who take CRM seriously are the ones RevOps leaders notice first.
Start asking why things break: Why did that deal fall apart? Why is conversion dropping at stage two? Why are customers churning after six months? That curiosity is what RevOps leaders look for when identifying who moves up.
Build relationships across departments: RevOps touches sales, marketing, customer success, product, and finance. Athletes who take time to understand how other teams work build the cross-functional perspective RevOps requires.
Learn the tools: Salesforce, HubSpot, Looker, Tableau, Outreach, Salesloft. You do not need to master all of them. But showing familiarity puts you ahead of 90% of candidates.
FAQs About Revenue Operations Careers
What is revenue operations?
Revenue operations is the team responsible for aligning sales, marketing, and customer success around shared goals, systems, and data. RevOps owns the CRM, pipeline reporting, forecasting, and the strategic insights that help a company grow. It is one of the fastest growing career paths in tech.
Can athletes transition from sales into RevOps?
Yes. Most transitions happen after 18 to 24 months in a sales role. SDR and BDR experience builds the foundation because you learn CRM systems, pipeline management, and how sales teams operate from the inside. Athletes who show curiosity about data, systems, and cross-functional processes are natural candidates.
How much do RevOps professionals earn?
Compensation ranges from $55,000 to $90,000 at the analyst level, $100,000 to $235,000 at the manager level, $140,000 to $215,000+ at the director level, and $180,000 to $400,000+ at the VP level. Growth-stage companies often include equity on top of base compensation.
What does a RevOps leader look for when evaluating reps?
CRM hygiene, pipeline math knowledge, forecast accuracy, and the ability to book next steps consistently. Reps who know their own numbers, forecast honestly, and treat their CRM as game tape stand out. Reps who confuse activity with progress or fall for happy ears get scrutinized.
What is the most important habit for a new SDR?
Never leave a sales call without booking the next meeting while still on the line. Data shows reps who do this have a 90% show rate and hit quota at three to four times the rate of reps who follow up by email to schedule. It is the single highest-leverage habit a new SDR can develop.
Ben went from a rugby pitch to a hospital bed to a sales floor to a police cruiser to leading revenue operations at a company managing billions in assets. The path was not straight. It did not need to be.
The Free Agent Sales Combine is where athletes get access to people like Ben. Leaders who have been in your shoes, built careers on the other side, and are willing to come back and tell you everything nobody told them. That is what this community is built for.
Join the network at gofreeagent.com.