Data Protection + Honesty-as-a-Service I Enterprise Sales at Rubrik

I am fortunate to spend my days helping people to solve problems that positively impact their professional lives and their organizations.

When I am not working, you can find me with my family at the beach or in the mountains. I enjoy camping, snowboarding, fly fishing and attempting to golf.

I am pumped to announce that I am moving into the role of VP, Sales here at Schellman.

The last 7+ months have been an amazing experience and I am excited to continue working alongside Preeya Voss and our entire sales, GTM, delivery and leadership teams. 

I am grateful for the trust in me and the opportunity that has been provided.

From the top down Schellman operates in transparency and in a way that continuously prioritizes what is best for our clients, prospects and the people who work here. 

2026 is poised to be a big year for Schellman and we are hiring for multiple roles across sales and GTM. Check out our careers page and shoot me a message if you are interested. 

In the meantime, I am looking forward to continuing to help global businesses to meet cybersecurity compliance requirements that fuel their GTM growth. 

Onward and upward.

Jacob Karp

Sales Leadership at Schellman I Cybersecurity Compliance and AI Governance + Honesty-as-a-Service

I’m a 40-year-old seller who has generated +75% of my own pipeline over the last 10+ years. 

I say this because it’s come to my attention that there’s a misconception that longer tenured or higher segment sellers don’t prospect. 

This couldn’t be more wrong. 

No matter my age and tenure, the need to self source pipeline has not changed.

Because I’ve yet to meet a seller who regularly exceeds their number relying on others to bring in the majority of their pipeline.

Pipeline generation never stops. 

But I do think it starts to look different the longer you are in this role.

Heres how I strategically prospect after 12 years:

- Deep account research and lower level converstions to create a POV to send to VP and C-suite 

- Writing ghost notes for my executives to send to prospect execs for alignment 

- Enabling partners to sell on my behalf, by helping them understand our value prop and my POV on accounts 

- Seeking out referrals and warm intros anywhere I can 

- Finding past customers or users in my prospect orgs to engage with 

- Working with my marketing and sales dev org to focus on key targets and operate in tandem to generate pipeline 

- Coming up with creative campaigns and personalized gifts to send to execs 

- Trying to get people out to events and in person 

- Attending industry events and conferences and tracking people down Iive

- Sharing relevant industry insights, articles, podcasts and learning opportunities 

None of that is rocket science. 

The reality is, while I may have far less volume in my outreach, my intent is still the same: set meaningful meetings with key stakeholders that lead to pipeline that will convert and revenue that will close.

And that doesn’t change regardless of age, tenure or segment.

Here is a full breakdown of how I generate pipeline: https://lnkd.in/g7hTH77r

Each time someone on my team books a meeting, I call it out in our team channel as fast as I can. 

A shoutout, some info and details around who, what, where, how. A learning, a nugget or tidbit on what worked and why. 

It is one of the first thing's I put in place in my new role. 

Not because I am a genius sales leader (lot's of learning and work to do to figure out how to be that, if ever). 

But because I did that job for 12+ years. I know how hard it is to book a meeting. 

I know what it takes to do the research, create the messaging, find the right people, respectfully and professionally reach out to them across channels, follow-up with added value. 

And then to do that at scale, day in and day out. Often in the quiet, by yourself, with your mind working against you.

So every chance I get I want to celebrate the little wins. 

That momentum matters for the person who booked the meeting as well as the team. 

And honestly I enjoy doing it, it is the least I can do for a job well done.

Onward and upward.  

#karpediem

In late 2018 I entered the holiday break knowing I was likely going to get PIP’d and laid off after the New Year.

It was my first year in software sales and I had had no real success to speak of.

There were GTM, territory and product issues at play, but I was also part of the problem. Maybe one of the biggest parts.

I was arrogant, unwilling to listen and didn’t take coaching well. I had been successful as a seller in another industry and wasn’t willing to adapt to my new industry.

I finished that fiscal year with my lowest attainment of my career and a month later I was PIP’d and laid off. 

I spent a week sulking and being upset about everything. I considered going back to my old industry which would have been the easy route.

After a lot of reflection, I decided I wasn’t going to give up and wanted to prove I could make it in the world of software sales. 

My resolution that New Year was not a resolution, but instead a list of all the reasons I had failed with a focus on the ones I could control. Mainly being coachable, moldable, adaptable and realizing I had a ton to learn.

The biggest thing I did was that I checked my ego at the door. 

The next year of my professional life and the subsequent years since haven’t been easy, but they have been the most impactful of my career. 

I enter 2026 in the best position of my career.

If you’ve read this far, the intent of this post is not a humble brag. 

It’s simply to keep going and keep pushing. Things won’t always be easy. You may have to admit to and accept all the things you need to do better. 

Luck and timing will play a part (I’ve certainly had both), but you are the difference. 

Go make things happen for yourself in 2026.

#karpediem

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A couple weeks ago I received some much needed coaching. 

Not in regards to my new role, but instead for the one I had spent 12+ years doing and working to perfect. 

A role I considered myself pretty capable and experienced in. A role I am now tasked with leading.   

The coaching was completely valid, deserved and timely. 

As I was transitioning out of my role as a seller, I was still overseeing some strategic sales cycles. One in particular had been ongoing for months and wasn't moving as fast or quite like I would like. 

My outreach started to get lazy and I began doing things I knew I shouldn't. Things like "checking in" and "just following up" and asking for their time. Things I have long known I shouldn't do in that way. 

Me focused activities, with no value add for the prospect. Just ask after ask. 

And so, the coaching and feedback was: "think about the give, give, give...then ask." 

Or as I had been taught previously: "deposit, deposit, deposit...withdrawal."

All I could say was that I totally agree, I knew better and appreciated the reminder. And then we course corrected. 

Even after 12 years I still need reminders of how to do this job the right way. And it was perfectly timed as I transition into my new role and think about the way I want to lead. 

No matter how long we do these jobs, the fundamentals don't change. And neither should our ability to receive coaching, regardless of tenure or level in an org. 

Thanks to Preeya Voss for holding me accountable and the coaching. 

If you want to work in an org that prioritizes this type of leadership, we are hiring. 

#karpediem

If you are planning to "circle back" starting next week, do your audience a favor. 

Provide a short summary and context for the outreach. 

Remind them (and yourself) what the previous conversations were, where things stand and next steps that both sides need to accomplish. 

You can do this in a short couple of sentences or bullets to help bring things back up to speed. 

Because most of us can't remember what we ate or wore two days ago at this point, let alone a sales conversation we had the week of 12/15. 

And when you get back on that first call, use the "What We Have Heard" slide if you have it. 

That looks something like this:

Title: What We Have Heard 

Bullets to summarize:
 - Past conversations and key initiatives
 - Current state and preferred outcomes
 - Gaps and risks today (good place for bold font and highlights)
 - Next steps 

(Pro tip: this can also be the email format)

I will be doing this for my prospects and clients and hopefully they will do the same for me. 

I've had too many cookies, watched dozens of hours of Bluey and also have every song from Gabby's Dollhouse ringing through my head.

I need some reminders.  

Good luck. 

#karpediem

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