👩🏻‍🏫 Krysten Conner

🚫pipeline anxiety l Terrible dancer l Always a Teacher 🦄🦄🦄 ex Outreach, Salesforce, Tableau 👉🏼👉🏿👉🏽 Click bell/top right to be notified when I post 🔔

You’re not trying to “hit quota.”

You’re trying to become the kind of seller who can repeat top performance across territory changes, market shifts, and new quarters.  

Not with luck. Not with late-quarter heroics. With a *system*.


Most AEs can have a great quarter.  

Consistent top performers have a way of operating that creates sustainable, repeatable results.

That’s what I teach.


I spent 12 years selling Enterprise deals at Salesforce, Tableau, and Outreach. I eventually broke records, 14X’d territory expectations, and ran a 47.6% win rate. But I didn't start that way.

The biggest shift I made wasn’t a new script or a new tech stack.

It was learning how to sell like a top performer actually sells:

✅Reduce confusion (connect the dots, make WIIFM obvious, reduce friction)
✅Run discovery that’s **direct and tactful**
✅Multi-thread early and build real champions 
✅Win the 95% of the sales cycle that happens between meetings
✅Act like a **Sherpa**: guide the buying journey so your buyer never has to guess what’s next


If you’re a rep who’s already performing and you’re thinking:

“I don’t want to be a one-hit wonder.”  

“I want to be on the leaderboard… consistently.”  

“I want make my process sustainable, so my results are sustainable.”

I'm your person.


Here’s what clients say after working together:
 👉 “I closed a $2.66M ARR enterprise deal after 26 months of work, and Krysten's coaching was critical in helping get it across the line."
 👉 "I set an ambitious goal when I started: hit at least 200% of quota in my first full quarter. Working with Krysten helped me turn that goal into reality. I hit 225% and closed the largest deal ever won by a new rep."
👉 "Wanted to thank you and let you know I closed my biggest deal ever in December, $2.2mil TCV, 3 year agreement. We were stuck at one stage with a start date that would have caused the deal to slip from Q4 to Q1, I used your COI principles and in-particular a visual graph that showed what the actual cost was of starting now -vs- later. Ended up getting it done 🤩 Thank you!!"


You don’t need another sales theory.
You need someone who’s been in your shoes - and knows how to win big deals now.

Let’s work together: krystenconner.com


🟢 I offer 1:1 coaching for individual reps, and workshops for sales teams who want to win bigger, faster, and more often.


Browse client wins here: https://www.linkedin.com/in/krystenconner/details/recommendations/



💫"We pay for every lesson with either time or money. And we use the currency we value least."
         -Alex Hormozi

Member

I walked away from the biggest deal of my career. $13.7M. Would've blown my quota out of the water.

But here's what that "loss" taught me...

The CEO had everything: 
✓ A problem we could solve 
✓ Agreement he HAD the problem
✓ Desperate need to fix it 
✓ Budget approved

But one thing kept nagging at me.

Every meeting, he'd ask about customization. 
About "partnering" to build features.
About source code access. 

Classic Build vs. Buy syndrome.

After our 5th in-person meeting (yes, FIVE), I finally saw it clearly.

This wasn't a buyer. This was a builder trapped in a buyer's process.

His personality screamed "I'll do it myself." 
His energy peaked when discussing his team's capabilities.
His questions focused on HOW we built it, not WHAT it could do. 

So I made the call that physically hurt:

I removed it from my pipeline.

My manager: "Are you SURE?" 
My financial plan: "But the commission..." 
My ego: "You're giving up."

Here's what happened next:

→ Freed up 30+ hours that month 
→ Focused on a $1.8M deal that actually wanted to buy 
→ Closed 3 other deals while he was still "evaluating" 
→ Finished with my best year ever

And that CEO? 
18 months later, still building. 
Still solving the same problem.

The real lesson?

Not every deal is YOUR deal.

Some buyers aren't buyers—they're builders in disguise. And the time you waste convincing them is time you could spend closing real deals.

Three questions I now ask myself:

1./ Are they asking about outcomes or architecture?
2./ Do they light up more about building or buying?
3./ Is their real goal independence or results?

If the answers point to "building," I'm out. No matter the size.

Because the best deals aren't always the biggest ones. 
They're the ones that actually close.

What deal have you walked away from that taught you the most?

Krysten Conner

I help AEs win 6-7 figure deals to overachieve quota & maximize their income l ex Salesforce, Outreach, Tableau l Training B2B Sales teams & Individual sellers l 3x Top 100 Most Powerful Women in Sales by Demandbase

Here are the 8 questions CFOs ask before every software purchase. (And they're brutal.)

Every champion I've ever worked with eventually hits a moment of panic:
"What do I say when Finance starts asking the hard questions?"

👉 Most CFOs won't tell you what they're really thinking. They just kill your deal silently.

But I've spent 13 years watching Enterprise deals die in Finance. And I've learned what CFOs actually need to hear.

Here are the 8 questions every CFO is asking behind closed doors, courtesy of the "Only CFOs" newsletter, as highlighted by  Nate Nasralla :

1. Why do we need [X product] now? We were fine before. 
2. What bucket does this fall into, and can you quantify it?
-----Improves efficiencies
-----Increases revenue
-----Mission critical (e.g. cybersecurity)
-----"Candy": nice-to-have tool that doesn't really fit into the above groups 
3. Is the spend in the budget? If not, how will you make up the difference? 
4. How does this tool tie into our company objectives for this year? 
5. What tools do we already have that do something similar? And if similar tools exist, why can't we use those? 
6. Implementation: What are the people / time requirements? 
7. Support costs: Will we need to upgrade soon to enterprise /other tier? 
8. Pricing:
-----If usage-based pricing: I want a detailed analysis on how pricing works and modeling for what our planned usage will look like.
-----If seat-based pricing: I don't want to buy a bunch of extra seats for planned growth. That got a lot of people in trouble when headcount growth halted and layoffs happened.

The deal-killers? Numbers 1, 3, and 5.

At Salesforce, I watched 6-7 figure deals die instantly when the champion couldn't answer those 3 questions clearly.

What are the best way's you've found to prepare your champions for these conversations?

Which of these questions makes your Champions the most nervous? 

PS - Find this helpful? You might like my newsletter. Over 7,000 sellers getting valuable nuggets every week. More details in my bio. Hope to see your name on the list!

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.

Jacob Karp

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.

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

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

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