Doug Camplejohn
(00:00)
Hello everyone, this is Doug Camplejohn and welcome to Revenue Renegades. In this episode, I’m excited to welcome Mark Kosoglow, the CEO and founder of Operator. Mark, welcome to the show. I recall when you were running sales at Outreach and at my last company, Fliptop, we had some early calls and interactions.
Mark
(00:15)
What’s up?
Doug Camplejohn
(00:29)
I’m excited to see you take on the CEO and founder role at Operator. Tell us about the company and the founding story. How did Operator come about?
Mark
(00:41)
Doug, we’ve crossed paths a few times. Fliptop was our first case study at Outreach. I’ll never forget visiting your office with Jess and filming the case study on an iPhone balanced on four cardboard boxes. The results were amazing, and that experience inspired Operator.
Mark
(01:10)
I was the first employee at Outreach and led sales to about $230 million. Then I became CRO at Catalyst because I believed post-sales was where investment was moving. Everyone talked about it, but few were willing to invest. It was a challenging space. I also remember Gainsight’s CEO, Nick Mera, who truly supported his team over many years. When I was leaving Catalyst, Max Altshuler—founder of GTM Fund and Sales Hacker and someone I worked with at Outreach—asked what I was going to do next. I mentioned consulting and advising, and he suggested incubating a company inside a GTM fund. He proposed an idea around contact data and even asked if I wanted to be the CEO co-founder. After talking to about 50 people in a few weeks, I developed a clear vision and solution. We raised money with Primary Ventures and, through 700 conversations since the end of July, I now understand this problem space extremely well. I believe our solution will close a significant gap that many organizations face.
Doug Camplejohn
(03:31)
That’s a great background. Max is a smart guy—he really knows how to pull the puppet strings. One phrase you coined when Operator launched was “the great ignore.” Tell me what that means and how Operator addresses it.
Mark
(03:56)
Industrial sales outreach at scale has led to what we call the great ignore. Essentially, instead of getting valuable responses, we’re just shouting into a vacuum. People tend to ignore the bulk of emails in favor of the few that matter. While it isn’t entirely black and white, the reality is that you can buy attention in bulk with flashy tools and AI. For example, a startup post on LinkedIn can drive traffic to a webpage, triggering an email from a vendor—even if the recipient isn’t interested. Operator takes a different approach by building relationships and solving real problems. Our multi-agent system first studies your company to identify key metrics and value propositions, then finds customers with corresponding problems, and finally crafts highly targeted messaging. Imagine having a follow-up email so precisely tailored that it feels like an individual discovery call—that’s what we call audience-of-one messaging.
Doug Camplejohn
(06:05)
So what does onboarding look like for your customers? Do you scrape their website, ingest their help center, or conduct interviews?
Mark
(08:19)
Many AI platforms require extensive manual setup. When a customer comes in, I simply use their domain to run our system. We first create a contextual profile to understand who they are. During onboarding, we adjust details—if they prefer three value propositions instead of four, or a different way of expressing a metric. This refined profile informs our messaging, ensuring the tone and calls-to-action match their preferences. Then they’re ready to roll.
Doug Camplejohn
(09:28)
Got it. Can you share some examples? I know you’re still in stealth, so feel free to be cautious, but I’d love to hear anecdotes about how people are using the platform and the results they’ve seen.
Mark
(09:41)
Sure. I’ll read an email generated for one of our customers. It was written for a company that helps hire software engineers faster and more accurately, and it was targeted at Lyft.com. This email was generated entirely by our system using only the customer’s domain and Lyft’s data—even before full onboarding. The email stated:
“Doug, your engineering team spends 12.5 hours per technical hire—25% above the industry average—with a 35-day hiring cycle. With 140 planned tech hires, your team will spend 1,750 hours on interviews this year, equivalent to losing an entire engineer’s productive time. We helped Unity reduce interview time by 50% while maintaining quality, processing 750 candidates in 90 days.”
Let me explain. The 12.5 hours per hire came from our feature called exhaustive citations—we match every metric with a source. For instance, one citation was an interview guide on Lyft’s website that detailed each step’s duration, which added up to 12.5 hours. Another citation provided an industry benchmark of 10 hours, showing that 12.5 hours is 25% higher. Our system determined a 35-day hiring cycle using Glassdoor reviews and analyzed job listings to find 140 open positions, leading to 1,750 total hours. The system then generated a sentence quantifying the lost productivity—equivalent to an engineer’s full year.
Doug Camplejohn
(13:10)
That’s incredible. How do you see this fitting into the existing stack? Is it a replacement for current tools?
Mark
(13:21)
Most contact data is bought to secure meetings, but there’s a huge gap between having data and actually booking meetings. We’ve closed that gap. For one customer, we offer blocks of 10 accounts—each account includes three personas (for example, head of marketing, demand generation, and sales). For each persona, we provide all available contact data along with three common business problems they face. That gives you up to nine business problems, and for each, we supply an email draft, a LinkedIn DM draft, and a cold call conversation starter. In total, you get 27 high-quality touch points.
Doug Camplejohn
(14:37)
That’s amazing.
Mark
(14:52)
Doug, you never have trouble getting your first 10 customers. Our approach is much more precise.
Doug Camplejohn
(14:58)
The level of noise in traditional outreach is just too high. I love what you’re doing. Let’s talk about go-to-market. You scaled Outreach to over $200 million—what lessons from that journey have you applied to Operator, and what are you doing differently?
Mark
(15:21)
First, I believe in being honest—I only sell what we can deliver right now. We have plans for the future, but I never over-promise. Secondly, I learned from my time at Outreach. I remember working with Jeff Serlin, the former head of ops at Marketo, who showed me his detailed financial and organizational planning. He taught me that once there’s not enough social proof, customers lose trust. For example, he implemented a one-month opt-out before locking in a 12-month contract, which converted 92% of contracts and boosted revenue. At Operator, we use a “prove-it-to-you” contract model that allows customers to test our product without a long-term commitment. If you’re confident in your product, you shouldn’t worry about customers opting out.
Doug Camplejohn
(17:45)
I love that approach. You’ve also written about creativity in sales. How do you foster that in your team?
Mark
(17:53)
Many people limit their creativity out of fear of failure. I once read The Little Red Book of Selling by Jeffrey Gitomer, which encourages you to be yourself and take bold risks. For example, when selling to schools, I bought 200 suitcases, filled them with our materials, labeled them with a special deal, and dropped them at school doors. That unconventional approach secured about 150 meetings. I even once gifted early-blooming crocuses to school secretaries, which generated excitement. As a 1099 employee on commission, failure was entirely on me—this pressure pushed me to take calculated risks. I encourage my team to discuss and learn from risks openly.
Doug Camplejohn
(18:46)
I recall you once mentioned you had a new hire sold pizza on their first day. Is that right?
Mark
(21:18)
Yes. At Outreach, our SDR team was given a list of about 20 companies in Seattle during their first week. Their task was to call these companies and sell pizza for lunch. Although results varied, the exercise taught them to handle rejection and learn from their worst calls. They even had to call five executives at our company to try to book a meeting. It was real-world training.
Doug Camplejohn
(23:05)
What effective methods have you seen for ramping and training sales reps?
Mark
(23:13)
Ramping is challenging. I once developed a detailed ramp program that started with defining the ideal candidate. Then I implemented a daily routine: at the start of each day, each rep shares the three tasks they plan to accomplish, and at day’s end, they report on their progress. This daily accountability helps steer them in the right direction.
Doug Camplejohn
(24:55)
What is the typical trial period to determine if a rep will succeed?
Mark
(25:01)
I believe success comes down to two things: the rep’s effort and the manager’s execution. I pay a base salary for a defined level of effort—whether that’s 100 or 1,000 cold calls a day. If a rep doesn’t put in the required effort for a month, I would put them on a performance improvement plan. However, if the rep is trying hard but isn’t producing results, then it’s on the manager to adjust their strategy. Over time, if a rep can’t be coached despite solid effort, it’s time to let them go.
Doug Camplejohn
(26:28)
That’s a great segue. What traits separate an average sales leader from an exceptional one?
Mark
(26:40)
Street credibility is essential. Reps need to trust that you’re willing to step into the trenches. I built my credibility by joining cold calls—once, I made 100 cold calls in a day at Catalyst just to show my commitment. At Outreach, I even took over a rep’s tasks for a week and recorded how I handled 50 tasks in 30 minutes. That hands-on approach builds trust. Also, the depth of relationships you form is crucial; the stronger the relationship, the more you can ask of someone. I made it a point to congratulate every rep on a deal over $10,000 with a personalized Slack message, which reinforced our bond and motivated the team.
Doug Camplejohn
(29:19)
Hahaha.
Mark
(29:35)
That practice really boosted our quarterly performance.
Doug Camplejohn
(29:43)
Fantastic. AI is everywhere today, and many are exploring AI SDRs and AI in marketing. How do you see AI affecting leadership?
Mark
(29:48)
AI has amplified the urge to emulate what others are doing. My LinkedIn feed is full of posts showcasing innovative AI projects. Initially, I felt inadequate, but then I realized that just because I can do something doesn’t mean it fits my style or sales approach. We risk becoming nothing more than spam cannons if we follow trends without thought. At Operator, we strive for efficiency while maintaining genuine engagement.
We must focus on what our customers truly need rather than bombarding them with 40,000 emails that yield only a 1% reply rate.
Doug Camplejohn
(32:15)
More of Operator, less of that approach.
Mark (32:22)
That’s right. We aim for consistent efficiency, although we’re not there yet. I remain cautious of some AI trends on LinkedIn—they can be dangerous.
Doug Camplejohn
(32:44)
Looking back on your career—from selling shoes at the mall to leading global sales teams—what mistake taught you a pivotal lesson?
Mark
(33:02)
In my first outside sales job selling to schools, I once had an aggressive goal during a two-and-a-half-month selling period. Halfway through, I hit my goal and started getting meetings late at night in central Pennsylvania. As a family man, I didn’t want to miss time with my family, but I felt compelled to attend out of fear of losing future opportunities. I revised my approach by clearly stating my method and offering alternatives. In the second half, I signed up more customers than in the first half. I learned that desperation leaves a distinct odor and that selling should be about helping customers make confident decisions rather than forcing a sale.
Doug Camplejohn
(34:59)
That’s a great lesson. I often compare great salespeople to waiters who guide you to a rare find instead of pushing the most expensive option.
Mark
(35:21)
Exactly.
Doug Camplejohn
(35:29)
If someone pushes a solution that isn’t right, they aren’t truly helping.
Mark
(35:34)
My key message to salespeople is: your job isn’t to sell; it’s to help people make confident decisions. When you do that, three outcomes occur: you close the deal; if they choose someone else, it’s the right decision for them; and if they choose wrongly, they come back because they trusted you. In every scenario, the customer wins.
Doug Camplejohn
(36:16)
Fantastic. Looking ahead five years, how do you envision a salesperson’s day-to-day life?
Mark
(36:35)
I expect salespeople will spend more time in meetings and preparing for them. AI might assist with many tasks, but it can’t yet conduct a meeting. At Outreach, we streamlined our outreach using defined sequences. My hope is that we’ll spend less time on administrative tasks and more time making our customer interactions effective.
Doug Camplejohn
(37:31)
Before we wrap up, if you could automate one task in your life forever using AI, what would it be?
Mark
(37:44)
I have a specific follow-up system. I review the top three problems a customer mentions and use a task system in HubSpot that assigns a next step for every deal. If a CRM could automatically create these tasks, it would be ideal.
Doug Camplejohn
(38:35)
We’ll talk offline about that. That’s a good one, Mark.
Mark
(38:38)
That’s the one I’d automate.
Doug Camplejohn
(38:43)
Just to be clear, this isn’t a pitch. As a fellow Pennsylvania boy—I loved the Crocus story; I grew up in the Poconos—what’s something you’re passionate about that might surprise people?
Mark
(39:00)
I doubt I have anything surprising. My top priority and identity is being a father. I love spending time with my kids—they are my best friends. We do fun things together. Whether it’s a neonatal intensive care unit nurse saving babies, my daughter leading marketing in San Francisco, my son at Temple, or my high schooler, our time together is invaluable.
Doug Camplejohn
(39:56)
I love that. My youngest is 21, almost 22. It’s incredibly rewarding to watch them grow and share life experiences together.
Mark
(40:12)
I took all of them—and some plus-ones—to Portugal this summer. It was the best trip I’ve ever had. One surprising skill of mine is maintaining the best yard in the neighborhood. I guarantee my edging and mowing are better than 99.9999% of people’s.
Doug Camplejohn
(40:42)
Guaranteed it’s better than mine because I have zero yard.
Mark
(40:45)
Hahaha! Sometimes I step away from SaaS and B2B sales to relax, listen to a sports podcast for an hour and a half, and make my yard beautiful. That’s my weekly mental break.
Doug Camplejohn
(40:59)
I get it. So what is one thing you can’t live without in your daily routine?
Mark
(41:10)
I rely on my three-monitor setup; my productivity drops significantly without it. I have one monitor for my laptop, one for communication (Slack, iMessage, Spotify), and one for my browser, CRM, calendar, LinkedIn, and LogSeq—my personal knowledge management tool. This arrangement is essential.
Doug Camplejohn
(41:58)
Your Bloomberg terminal—your mission command center. I love it. And finally, how can listeners keep in touch with you?
Mark
(42:33)
I post daily on LinkedIn. It’s the only social platform I use and the best way to reach me.
Doug Camplejohn
(42:59)
Mark, I loved this conversation. I’m excited for the official public launch of Operator. Thanks for your time.
Mark
(43:10)
Thank you, buddy. Great seeing you.
