Conversation with a Sales Pro
OJ Cherry, CRO at StikeReady
Real conversations with the people who built careers on cold calls, hard lessons, and figuring it all out as they went along.
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OJ Cherry
OJ stumbled into sales almost by accident, mistakenly placed in an interview room where he caught the interviewer's eye and crushed it. He interned at Sophos during college, then spent 17 years working every role imaginable up to VP of Enterprise Sales. He then joined Binary Defense as CRO for two years before recently taking the helm as CRO at StrikeReady. Connect on LinkedIn.
Ian Thiele
Ian has been mastering sales since his college days working the Costco Membership desk. Today, he helps sales teams scale their outbound process from the comfort of his Herman Miller chair. When he is not optimizing pipelines, he is grinding to get his golf handicap down to a 10. Connect on LinkedIn.
The Conversation
You used to text prospects when everyone else was emailing or calling. Is doing something unexpected still the best way to get attention in this day and age?
I firmly believe it is better to burn out than fade away. A win for me is just getting their attention and being memorable. It does not always work, and sometimes that attention comes through frustration, but a completely generic touch is just a waste of time. "Hello, okay, goodbye" is just a numbers game. That is not effective.
The real question is: how do you change a predetermined outcome? When you cold call someone, 99.9% of the time you are going nowhere. So how do you change that? It is the same in a deal. Sophos was never the obvious choice on paper. Nobody walked in saying "I am buying Sophos." You had to shift the trajectory. That is the whole game.
"It is better to burn out than fade away. A completely generic touch is just wasted time."
OJ Cherry, CRO at StrikeReadyWhat is still the hardest part of B2B sales, then or now?
Getting someone's attention. Getting them to say "I'd like to look at you." That has not changed. The channels shift, the noise levels change, but the fundamental challenge is exactly the same.
Your inbox must be flooded with pitch slaps and weird subject lines. Is email outreach still a valid way to reach people?
A very low percentage. I do not think I have responded to any. I genuinely do not remember the last time I did. It is not dead, but if that is your primary weapon, you are fighting uphill with a blunt sword.
LinkedIn feels like it has shifted too. I get five connection requests a day followed immediately by a pitch. Is it still one of the best ways to find business?
It is more of a recruitment tool now. People do not really respond to sales outreach on there. I think of it as being for jobs, not for sales. The one LinkedIn message I would respond to? A young person genuinely asking for help. That cuts through because it is real and direct. The pitch disguised as a connection request? Immediately ignored.
You are building a new sales team at StrikeReady. What separates the rep you are replacing from the one you would actually want to hire?
In a complex sale like cybersecurity, it is tough to convince me you can sell it if you have not sold something similar before. Industry knowledge is critical for credibility.
Beyond that, you only need three or four deals to hit your number in this space. Having people you can actually call is far more valuable than being fed a list of 50 leads by a big company. I need independent thinkers. Creative people. Not someone who needs everything handed to them before they can execute.
"You only need three or four sales to hit your number. Who you can call is more important than how many leads you are given."
OJ Cherry, CRO at StrikeReadyTurnover is one of the biggest problems in sales. How have you managed to keep it low?
It was not luck. It was trust and money-making. When your team trusts you and they are earning well, they do not leave. The turnover I did have was mostly good turnover: promotions or necessary exits from wrong-fit hires.
And here is something that never shows up on a spreadsheet: you can replace me with a person, but you cannot replace 17 years of inherent knowledge and relationships. Turnover has a downstream impact that does not surface until it is already too late.
Was it a tough decision to leave Sophos after 17 years?
Not at all. I did not have anything more to learn. I kept making money, kept moving up, liked what I was doing, but I had hit a ceiling. The first year at StrikeReady felt like five years at Sophos in terms of what I got out of it.
Everybody is replaceable, including the CEO. Growth requires friction. If you are comfortable, you might be stagnating.
What is the one piece of advice you would give someone who wants to break into cybersecurity sales fresh out of college?
Ask for help. You are not getting in without someone getting you in. Learn to leverage relationships, the ones you already have, and go make the ones you do not.
Then start building your Rolodex from day one and actually stay in touch with people. I meet people all the time who say they want to connect, I offer to help, and I never hear from them again. That is a massive missed opportunity.
The second sale to someone is so much easier than the first, but only if you stayed in touch. Find common ground. Their sports team, their city, a shared interest. A simple "Hey, congrats on the promotion" goes further than you think. That relationship network is probably my most valuable skill, and I could have built it far better early on.
"The second sale is so much easier than the first, but only if you stayed in touch. That relationship network is my most valuable skill."
OJ Cherry, CRO at StrikeReadyKey Takeaways from OJ Cherry
- Change the predetermined outcome. Cold calls and competitive deals are stacked against you by default. Be memorable. Do what others will not.
- Email and LinkedIn have real limits. Senior buyers rarely respond to cold email. LinkedIn is a recruiting platform now. Diversify your channels.
- In complex sales, relationships trump volume. You do not need 50 deals. You need three or four great ones. Your network is your pipeline.
- Hire for independence and credibility. In cybersecurity, domain knowledge is non-negotiable. You need reps who think, not just reps who dial.
- Retention is built on trust and income. Turnover is not a culture problem. It is a trust and earnings problem. Solve those and people stay.
- Stay in touch, always. The biggest career mistake in sales is letting strong relationships go cold. The compounding value of a warm network is incalculable.