Sales Leader Interviews: Mark Kosoglow

Sales Leader Interviews: Mark Kosoglow
Elise Hymes


The Who: Mark is the VP of Sales at one of the hottest and fastest growing tech companies in the valley, Mark has scaled the sales team to over 40 people.

The Profile: VP of Sales @

AH: We've all had to fire someone whom we thought would be a rockstar. I mean they CRUSHED it at their last job, so why wouldn't they do the same at our company?

MK: In my experience, experienced reps have become good at managing a pipeline and replacing what has dropped out. Unfortunately, that is a very different skill set than building a pipeline from scratch. When, for years, you have just stewarded your pipeline, you lose the grind, determination, and fortitude to build a pipeline from scratch. It's too much cold calling, too much rejection. Also, a great rep has stories, tribal knowledge, experiences he/she has developed over time that are not transferrable to a new sales role, in many cases. I, also, think reps are overwhelmed with new processes, systems, tools, and knowledge. Hard to build a pipe and learn all the new stuff when all you've had to do for years is manage a pipeline.

AH: Given that there is data to suggest that sales experience is not the end-all-be-all data point to predicting sales outcomes, why do you think so many hiring managers still use that data point as a crutch for building a sales team?

MK: Past performance is the only quantitative, hard evidence you have to predict an unknown future. It still needs to be used, must be used, but it can't be a crutch. Mike Wallace as an All-Pro receiver with the Steelers, but he sucked with the Dolphins and Vikings. Fantasy team owners thought he'd still kill it with those new teams just bc they looked at previous stats. Past performance indicates a high likelihood of potential, and if you don't have, at least, potential, success will be hard. So to answer directly, managers SHOULD look at past performance to see if a rep has potential to be a top performer.

AH: How does someone new to the industry identify the difference between a thought leader who is pumping out relevant content and someone who is pumping out content moreso because they are trying to build a personal brand?

MK: Haha - make them open up their shop and show you they practice what they preach. I'll BEG someone to come to our State College office and see that we use our tool 100%, we push the envelope of what it can do, and we are in complete alignment with anything I've ever said publicly about our process/results. If I want to "the other guys" (and I have people that I talk to who get to peek behind those curtains), they are running like anybody else, and eat their own dog food. We eat the dog food before we sell it. That's how you know the difference.  

AH: Mark you've been at this game for a while. In your own sales career, if you had to do it all over again, would you change anything? And why?

MK: I'd learn the value of shutting up faster.

I'd become a better student faster.

I'd see the value of negotiating well faster.

I wished I'd have understood how my expectations cloud everything I hear/perceive/distill/infer from a situation.

In the beginning, wish I would have just done what I was told, copied what the best did, and not think my way was better than the way of the experienced winners.

AH: Why did you get into sales and what has you continue staying in the game?

MK: I've sold since I was a kid. I sold in high school and college. I am good at it, and I heard that you should stay in your strengths. I love that the discipline is an art and a science. I get to use both sides of my brain. For me, sales was really the only route. I want my compensation to be based on my ability to win, not on a salary slot.

AH: You've had to hire a lot of people has you've scaled the sales team at Outreach. What are the traits that you look for in a candidate that are meaningful and translate to a successful hire?

MK: Well documented:

  1. Hard work - can't teach it. gotta have it. will you make 100 calls if it takes that to be successful?
  2. Desire to win - can't teach it. gotta have it. will you give up or will you push through?
  3. Audible ready - can you handle the on-the-spot decision-making required to help people see how you can help them
  4. POSSIBLE NEW ONE - can you talk shop? are you well-versed enough to add value to a person even if they don't buy

To be great at sales:

  1. Curiosity - best way to get focus onto the prospect. natural curiosity gets you to pain. pain gets you to paid.
  2. Effort - hard work (see above)
  3. Ability to make connections - you've got to be able to take what you know about your product and help a prospect connect their pain/challenge to it

AH: What's the biggest failure you've experienced in your sales career?

MK: My last job. I thought I had insulated my sales team from organization-wide layoffs. I thought I had driven us to results that would keep my people safe. I failed many of them as most lost their jobs in a strategic change. Horrible. 

I learned that your leadership and corporate strategy are things you can't control. If you are worried about the decisions being made and the people making them, RUN! Find smart, determined, gritty people that are more resigned to failures leading to success than blaming everyone else for bad ideas, decision, and strategy.

AH: If you could give one piece of advice to any entry-level sales person what would it be?

MK: Sit next to the best person, take them to lunch, find out what they do and do that exactly. Don't make it better, don't over think it. Just do it.

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