RVP, Sales @ Bullhorn - I talk about creating systems for sellers to scale your impact, not your hours

3 years ago, I was drowning...

As an RVP at a fast-growing tech company, my life had become an endless stream of:

• "Urgent" emails
• Back-to-back meetings
• And constant fire-fighting

Waking up early and working late into the night.

My phone was always buzzing with notifications.

To make matters worse, it was taking a toll on my family.

The breaking point:

Missing my son's jujitsu belt test.

Something I'd promised I wouldn't do.

That night, seeing the disappointment in his eyes, I knew something had to change.

I spent the next year obsessively learning, developing & testing different productivity systems that would allow me to:

• Still perform at a high level
• Stop feeling perpetually overwhelmed
• End working nights/weekends just to keep up

I started creating what I called "mini-systems"

Small changes that had a compounding effect.

What began as a quest to regain control of my calendar...

Evolved into an operating system that helped me recover 10+ hours every week.

More importantly, spend more time w/ family. 

I've started documenting my learnings & "mini-systems" and now share them with others through my content and weekly newsletter The Systematic Sales Leader.

My goal is to help as many sales leaders as possible avoid the same burnout I and so many others experience through tested and proven systems.

If you're curious to learn more, check my "featured section" for a few free resources.

Keith Weightman

👩🏻‍🏫 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!

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👩🏻‍🏫 Krysten Conner

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