Inside Kolide

How I Landed VP of Sales at Kolide

Harry Robinson

There’s something to be said about the “easy apply” job era. With the appeal of simplicity comes even more options, and in turn — much less effort. Why not apply to anything and everything if it only takes one click?

When it came to my turn to be on the hunt for a new job 18 months ago, I was thrown into a world I had not been part of since graduation. Previous roles came to me through my network. A few interviews later, and you’re in; not much to be done in terms of search.

I took the departure from my previous role without any backups. Beyond hitting a few of those “one-click applies,” I was in at the deep end and learning how to swim.

After a few weeks and a holiday or two later, it was time. Time to decide where I would spend hours every day, where I would say I worked when meeting people, and what would be at the head of my LinkedIn profile.

I sat at my desk and began my search.

Luckily for me, I knew my strengths. I didn’t know a lot about looking for jobs, but I knew sales. I’ve learned how to create an opportunity from nothing and ride it all the way through the close.

So, that’s where I started. I decided to treat finding a new job like finding a new B2B sales opportunity. In this article, I’ll share the five steps I took to close the VP of Sales job at Kolide:

  1. Ideal Company profile
  2. Target List
  3. Prospecting
  4. Qualified Pipeline
  5. Close

Step 1: Ideal Company Profile

Creating an ideal company profile starts with your “must-have” characteristics list. In this case, I noted all of the variables I wanted in my next role.

Here’s what I came up with.

I knew I wanted to be involved in sales for a B2B SaaS startup. I acquired a significant amount of experience in my previous role, but I left with an unfinished feeling. I had a plan I couldn’t follow through with — and I wanted to try again from the beginning.

My list of wants continued. I wanted a…

  • product designed for all users within a company
  • product with low cost per seat, but an enormous deployment opportunity
  • shorter sales process than Enterprise sales — to close deals more frequently
  • product first CEO

In addition to my want list, I added companies that would allow me to deploy my strengths: relationship-building and visionary action. I created a plan from this — I decided that to be successful and land a role that met my want list, I needed to get to the top.

I needed to get to a startup’s CEO and then paint my vision for them. Show them upfront that they were already missing something I could deliver. By not having sales, they were hurting sales, not just missing sales. My goal wasn’t to convince them they needed me. I wanted to convince them that they needed my profile to succeed.

I knew from experience and research that startups often get lured into thinking they need their first salesperson to be from big companies. They believe they need someone who works in large teams and can bring process, enterprise experience, and big logo chops. They’ll often get encouragement from their investors to follow this path.

The fallacy here is that the startup will go from $100K ARR to $100M ARR in no time, and they “need someone who can scale a team to $100M ARR”. This is faulty thinking. There are a dozen other phases between $100K and $100M.

The path from $100K to $1M is bumpy. Nothing is defined, you don’t yet have product-market-fit, and significant prospects can pull you all over the place like a small sailboat in a storm. Then from $1M to $5M, $5M to $10M, and so on. I would need to convince them they needed someone who had been at the stage they were at and the next.

Step 2: Target List

With my wants list and an initial plan created, the next step was to create a target list of companies that matched my vision.

Vision and easy-apply do not go hand in hand. My goal was to win over the CEO of a startup with my experiences and future plan. I couldn’t do this by filling out one “how many years of experience do you have?” field. I quickly knew that the “apply to anything and everything” approach wasn’t going to work for me.

A target list in B2B sales isn’t 100–200 companies that you send automated templates to. You take 10–20 aligned accounts. You research them, learn about them, and understand the stakeholders. You have to do this to understand their pain points — and how your solution can heal them.

I took these expectations in alignment with job searching. In the same breath, I could hit “apply” to 100 companies I maybe liked — I could concentrate on ten companies I knew I wanted.

The best part about staying concentrated on a few companies that I knew I’d be happy to be a part of is they didn’t even need to have a sales role open. My goal wasn’t to find their careers tab on their website and apply. My goal was to get to that CEO and show them what they needed before they even knew they needed it.

I believed that product-led CEOs would be so busy on the product/engineering side, they might not know when to hire for sales, and likely some were even intimidated by the prospect. I would make the process easy for them.

I won’t bore you with the complete list I came up with. The list was mostly made up of apps, companies, or solutions I’d come across that had caught my attention — and Kolide was atop of that list.

My previous company had recently deployed Kolide. It was the very first company-wide software that had been implemented at that 180-employee company. When I was asked to enroll in my company’s endpoint monitoring system, I was pleasantly surprised by the user-focused approach and the control of the device being left to the user. It was a system I believed in.

I recall chatting to the CTO about Kolide as we rolled it out, and he was visibly excited. He explained that we needed to sharpen our compliance game due to pressure from our largest customers, but he was very resistant to device management. He knew it would damage the engineering organization’s culture, which was a company asset too valuable to break.

Kolide, he explained, had this fantastic approach to messaging people through Slack to remediate their compliance issues. There was no new software for end-users to learn, no new portal to remember to access. It was all via Slack, simple as that.

I was excited. It was very novel, but felt so obvious when I thought about how much time I spent in Slack talking to all my other colleagues. It’s where I was spending my time and the best place to get hold of me if action on my device was needed. It was a brilliant collaboration.

Step 3: Prospecting

It took a few weeks, but I had my target list completed. It was time to research my marks. I started with Kolide, where I quickly found Jason, the CEO, on LinkedIn. As you would expect, I started with a simple LinkedIn message:

A screenshot of a linkedin message from Harry to Jason Meller. Harry's message reads: Hi Jason, Just wanted to say Kolide rocks - we've deployed it at Celtra and I'm really impressed. Would you love to hear more if you're open to talking? Harry.

A quick attempt to see if he would bite.

He didn’t.

After a week or so, I’d not heard back. Not defeated so quickly, I sent a follow-up message.


Now what? Luckily for me, there were multiple forms of social media. I decided to search around and see what socials Jason was active on — Twitter, it turns out. I decided to reach out to him there, a place he was probably not expecting prospective applicants to go. I sent him the following:

A screenshot of a Twitter DM between Harry and Jason Meller. Harry's messages read: Hi Jason, hope you're well. We use Kolide at Celtra and Jaka speaks highly of it. I like the approach to install through Slack. Curious if you might be in need for Enterprise Sales support yet? I'm exploring new roles. I've been with Celtra for 7 years and I am their primary Enterprise Seller. Have been CEO Overachiever for 3 of the last 4 years and I am an IT geek and aspiring lawn care expert. I also studied a Masters in Information Studies so think I'd be a good fit.


Jason wasn’t too chatty at this moment. I decided it was time for a more direct approach. With the power of the internet, I found his email. I wanted to add a bit more of my personality to this email. Feeling hopeful, I sent the following message along with my CV.

A screenshot of an email sent by Harry to Jason Meller. Harry's email reads: Hi Jason, I hope you enjoyed the long weekend. I've ping'd you a few times on Twitter and LinkedIn but know those can go unnoticed. I've learned the best way to get someone to give you their time to hear your pitch is to teach them something so he's my attempt to part some wisdom on you. I often see salespeople demo'ing too early in the deal. They'll qualify an opportunity and ping the pre-sales team asking for a demo before they've done proper discovery. Demo's without discovery are just guessing. At Celtra, I introduced the concept of selling the demo. The demo is special. It's the prospects' chance to see evidence of everything you've talked about. But in enterprise sales, demos don't sell. Product demos authenticate your pitch and therefore should be held as late as possible in the deal. Wait until you know budget is approved, wait until you have the executive stake holder in the room, wait until you've surface the pains they want to solve. Most of all, wait and build up that excitement so when they see your wow moment, the length of time between wow moment and them getting started is as short as possible. Don't burn your key product wow moments early in the deal before the prospect knows why it's important or why it's wow. With our sellers I always try to understand why they want to demo so early and unfortunately, all too often, the reason is that the prospect doesn't fully understand what we do and the seller is hoping showing a demo will enable the prospect to figure it out. This rarely happens; never risk a deal by expecting prospects to figure out our product's value. Looking at VP Sales Roles and think I could help Kolide!

No response.

Not to worry, it was time to deploy the infamous follow-up email.

A screenshot of an email sent by Harry to Jason Meller. Harry's email reads: Hi Jason, Following up on previous emails about a sales role at Kolide. I hope you had a nice weekend. The next chapter in my "enterprise sales tips series" - a working title. You probably already know better than to just give prospects the price when they ask. But what if they insist on it? "Just tell me the price already. There's no reason for you or me to waste our time going through this whole conversation only to find out at the end that your price isn't a good fit for our budget. So how much are we talking?" Sounds reasonable. So what do you do? Give them the price range? Let's assume for a moment you give them a price range:  "The price range is around $100,000 to $200,000 annually."  Congratulations, you may have just put the final nail in your coffin. At this point, you have given away all your power in the sales conversation. You know nothing about the prospect and by putting out your price like this, you've positioned our solution as a commodity. The prospect now looks at our offer as a cost center and it's very hard to establish the value of our product from here on out. Unless we are actually selling a commodity, you simply don't have the insights you need to quote a prospect a price. For enterprise SaaS like Celtra, you need to know a couple of things about your buyer, for example: -How much value is our solution able to create for this prospect? -How will that value be evaluated and quantified, which KPIs? -How much support does this prospect need? -What are their overall wants and needs? -What's their budget? -How much usage will they create on your platform? There are all kinds of ways that quoting them a price too early can backfire. Most people think that quoting a price that is too high is the potential deal breaker, and for many prospects this is true. But sometimes the opposite is true! What if the price is too low? Some buyers have gigantic budgets and want to know that you're a serious vendor. If you quote them $100k–200k a year for something that they usually would spend $2 million a year on, they won't take you seriously. You lost the deal because you didn't know who you were dealing with. So what should you do instead? If the prospect tells you they don't want to waste time talking about an offer that might not match their budget, just ask them: "Well, what's your budget? We have many ways to structure deals, so if you tell me your budget, I can tell you if and how we can make it work." Many prospects will share insights about their budget with you. But some won't ... "I'm not going to tell you my budget" Many sellers will freak out when they get a no from a prospect. "Oh no! I pushed too hard and now they're upset!" No. That's the completely wrong way of looking at this. You've elicited a strong response from the prospect. A moment ago, the temperature between you was cool, they were slightly interested. You've just turned the temperature up. Now the prospect is much more emotionally engaged. Take that energy and turn it into interest. That's how you turn a disengaged prospect into a hot lead in a sales call. Establish value first by gather relevant insights about your prospects. Then when it comes to price, you can make it about the value your solution provides. Rather than being a cost center, the prospect views it as an investment. The question shouldn't be: How much does this cost? The question should be: How much will the ROI of this investment be? Celtra's CMP is a premium product but if you want to position us as a premium solution, you can't do it with wholesale pricing. It's not a sustainable business, and people draw conclusions about the value they get based on the price you charge. Pricing is positioning. At Celtra, I advise our sellers to: Never give away price without understanding your prospect. Never give away your price before establishing value in a sales conversation. If you talk about price before you know what value you create, you're talking cost, commodity, you're losing control. When you talk price once you truly understand the prospect and customer, price is now an investment, it's branding, it's positioning. See how it turns from something negative and out of your control to something positive and empowering, something that strengthens your negotiations in the sales process. Looking forward to hearing from you. Harry

You guessed it. There was not even a brush off of a response.

A screenshot of showing u/jmeller is the moderator of the r/sandwiches subreddit

I knew that I hadn’t exhausted all my avenues, so I wasn’t prepared to give up yet. It was the salesman in me and the dedication to get the right role with the right company that was going to help define my career. It was worthy of pursuit.

Lastly, I searched on Reddit, where users have anonymous usernames and was able to piece together enough Kolide related comments to believe the admin of r/sandwiches was my mark.

So, I messaged the mod.

And I got nothing. I was running out of options, and quite honestly, my hope was dwindling.

My last play (short of going to his house, which definitely would not have gone well) was to go back to the CTO of my previous company and ask him for an introduction to his Kolide account manager.

This email followed:

A screenshot of an email sent by Jaka (the CTO of Celtra) to Antigoni Sinanis of Kolide. Jaka's email reads: Hi Antigoni, Hope you and Kolide are doing well. This time, I come to you with something other than a support question :). One of our enterprise sellers, Harry Robinson recently left Celtra and is looking for new opportunities.

I received the following back:

A screenshot of an email sent by Antigoni to Jaka. Her email reads: Hi Jaka, It's always great to hear from you! This is definitely an intriguing opportunity. We've been discussing hiring someone in sales/marketing to help us at Kolide for some time, and Harry sounds like he'd be the perfect fit. We've sort of put a pin in our hiring budget due to Covid, but I a very interested in connecting! Jason, our CEO, just went on paternity leave, but I think he will be interested as well. I imagine Harry is inundated with calls, meetings, offers, etc., but if he has time to chat, I'm very much open to it. Thank you for reaching out about this. I really appreciate it! I hope all is well with you. Talk soon, Antigoni

After a few back and forths with Antigoni, I finally connected with Jason.

A screenshot of a meeting invite between Jason and Harry scheduled for Tuesday August 18th, 2020 at 11:30am - 12:00pm EDT

And the rest, as they say, is history.

The lesson to take from this exchange is:

  1. Network, network, network, knowing someone by a few degrees can give you the credibility to change your entire career.

  2. You can find anything on Google, Twitter, emails, Reddit accounts…

Step 4: Qualified Pipeline

The first call with Jason was a hit. They weren’t looking for a sales hire, but I could see a way of convincing Jason that taking a sales hire earlier than expected would be a good thing. Next, it was time to work this opportunity through the pipeline to the close. I pulled out every sales tactic I had.

I filled my follow up emails with great SaaS sales content, not just self-bragging:

A partial screenshot of email from Harry to Jason. Harry's emails reads: Hi Jason, As discussed I'm excited to find my next 7 year adventure after a great time at Celtra. I learned most of what I know about SaaS sales at Celtra being fortunate enough to launch our brand direct efforts and selling deals from $200K to $2.5M to companies including Uber, Facebook, Spotify, Shopify, Square, Twitter, Kroger and others. Yet, the truth is, more deals closed lost than closed won - it's the way it is when you don't have product market fit and as a seller you are running the entire process from prospecting to qualification and opportunities. I probably wouldn't believe anyone who said they sold at start-ups and had a close rate over 50%. I love the craft of enterprise selling and whilst my only experience so far is creative software, from folks I've met, conferences I've been to and books I've read - the art of enterprise selling is typically universal and the most effective are able to: Tell great stories that captivate their audience and spark them to make change Qualify fast, focusing only on tasks that help them achieve their goals Help champions navigate their internal organization to get budget approval and executive sponsorship Focus not on 'MSA signed' but on the customer solving a problem...

Following my advice, I had sent Jason in my initial email; I didn’t demo too early. I saved my best highlights for when I sensed a moment of doubt:

A partial screenshot of email from Harry to Jason. Harry's emails reads: Hi Jason, You mentioned that the Kolide sell is very technical and it's likely most of my learning will be there. I probably won't bring a lot of understanding of the technical side of your prospects' problems with me. You're going to need to teach it to me but I can give you some insight into the sort of canvas you'll be working with. More interested in maths and physics than art and philosophy I'm technically minded by nature. As Jaka mentioned in his email: [harry is] The exact opposite of sleazy relationship-y "car salesman" archetype — he's geeky, hacks his home automation, loves technology, and loves bringing it into the right people's hands. Works *really* well with product & engineering to iterate on the product-market fit, has invented quite a few of our positioning narratives. I have an MSc in Information Management from the University of Sheffield which at the time was the number 1 information school in the UK. We covered modules including database design, information security, knowledge management, analytics and statistics....

Finally, I deployed my final weapon right at the end. Testimonial. My research surfaced a connection between Kolide’s primary investment partner and one of Celtra’s that knew me well. I timed this reference to go across shortly before meeting with Kolide’s lead investor at Matrix Partners.

A partial screenshot of email conversation between Harry and Joe Medved of Lerer Hippeau. Harry asks if Joe is connected to Kolide's lead investor. Joe replies that they aren't super close, but close enough to put in a good word if he needs it.

Most importantly, I used each stage to demonstrate my skills for the role.

On September 3rd, 2020, I received an offer to join Kolide as their first sales hire.

Fourteen months later, it has been a career-changing experience. I was right to stay focused in my job search. I am an excellent fit for Kolide — Kolide is an excellent fit for me. Now, I have the opportunity to do what I set out to do; bring my vision to life. Now, I have the chance to look forward to each new day working with Kolide.

How You Can Do It Too

When push came to shove, and I was sent to the job search world, I didn’t know what to expect. I started from the beginning, so I stuck to what I knew. I knew sales, I knew the process of creating an opportunity where there wasn’t one, and that’s what I did.

Here’s my advice on how you can do it, too. Make a shortlist of companies you are excited about, ensuring that each company needs what you are selling: your experience and your ability.

If a role only lets you use 50% of your abilities, you’re wasting 50% of what you can offer. The role I found at Kolide allows me to use 100% of my abilities, which leaves me feeling fulfilled and excited to give my energy to build a company that I believe in.

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