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

krystenconner.com

--> Pressure to hit your number got you lying awake at 2:41am?
--> Stressing over deals that are ghosting or slipping?
--> Burned out & feeling major anxiety?

Empowering tech sellers to close more complex deals is what drives me.

I spent 12 years in Enterprise sales as an Account Executive with multi-billion dollar tech companies like Salesforce, Tableau and Outreach. Along the way, I blew past performance goals in multiple roles.  Doing 14X what anyone had done in my territory, being #1 in new logo acquisition, and achieving a 47.6% win rate.

It wasn't always like that, though.

Early on, I couldn’t confidently qualify deals in or out quickly. I wasted lots of time on deals that didn't turn out to be real. My discovery felt haphazard, and I struggled to get prospects to go in depth or quantify their pain.

My first sales cycles were some of the longest on the team. Deals frequently slipped, and I got ghosted a lot. All which I felt powerless to change. I was always waiting for the customer. I didn’t know how to lead so buyers wanted to follow.

You might relate to feeling like I did: burnt out, anxious, and like you don't belong in sales. The sad part is feeling behind, scattered, and overwhelmed has become the new norm.

It took me over 10 years to gain the confidence, knowledge and skills that I needed to be a consistent top performer.

My mission is to ensure you get there faster - by sharing what I’ve discovered throughout my 12-year career.

My content and training has been featured by: 
--> pclub / Chris Orlob
--> 30 Minutes to President's Club
--> Kevin Dorsey / Live Better, Sell Better
--> Sell Better / Daily Sales Show
--> Outbound Squad
--> Challenger
--> Vidyard
--> RepVue

Here’s what my clients say: https://www.linkedin.com/in/krystenconner/details/recommendations/

--> Sign up for my newsletter for weekly coaching in your inbox:    krystenconner.com
--> Schedule a consult here:   https://scheduler.zoom.us/krysten_conner/coaching-consult

I help AEs win 6-7 figure deals to overachieve quota & maximize their income

pclub.io

Multi-thread Your Way to 34% Higher Win Rates 
Access multiple Decision Makers faster with proven templates & approaches
Expand your footprint and get "high and wide" access to multiple influencers in your top deals.

Sign up for the Multi-threading Masterclass here!

Course Author:  Multi-Threading Masterclass

Outbound Squad

Helping you pack your pipeline with qualified meetings.  Especially those shiny new logos.

Coach

Outreach

• 10-27% more revenue (Forrester study)
• 31% more meetings booked
• 29% more opportunities

Outreach is like Amazon for sales activities.  Makes everything about it faster & easier, more trackable, and you get better info for better decisions.  Frees you from mundane work. So you can do revenue generating work.

But don't take our word for it.  Adobe, Tableau, Zoom and 5,000+ other clients get extraordinary results with Outreach's system of action. Salesforce, Microsoft and SAP have all invested millions in Outreach.

Honeywell, Cisco and SAP drive predictable and measurable growth, increase efficiency + effectiveness of all customer-facing teams, and improve visibility into sales activity and performance with Outreach.

Enterprise+ Account Executive

Outreach:
• Forbes Cloud 100 for 2018-2020
• #1 in G2's Best Products for Sales, 2020
• $4.4B valued "Unicorn" 

Hustle + grit, being a decent human, and helping clients get what they needed were my 'few & vital'
 
Led to these results:
• #1 on my team and #3 in all of Enterprise for New Logo acquisition
• 711.21% YoY ARR growth in my book - all New Logo
• Top 3 rep in East region for new ARR, with 47.6% win rate 

Outreach optimizes every touch throughout the customer journey, managing interactions across email, voice and social.  Machine learning guides sales and service teams to take the next right actions.

Headquartered in Seattle but with offices in San Francisco, Tampa, and London, Outreach has received $289M+ in funding from top tier investors. **Backed by Salesforce & Microsoft** as well as Lone Pine, Meritech, Spark, DFJ Growth, Sapphire, Trinity, Floodgate, Mayfield, Premji Invest, Steadfast Capital Ventures, Sequoia Capital, Tiger Global Management Vista Equity Partners, Microsoft, SAP and Salesforce Ventures

Enterprise Account Executive

Tableau Software

How do you actually accomplish digital transformation, in real life? How have others built a data culture? What have they gained as a result of all that time and effort?

Working with clients to answer these questions helped me achieve: 
• 137.73% YoY growth in my book - this put me in the Top 7%; #5 out of 63 reps
• 145.36% of Services quota; #22 out of 63
•  41% partner attachment (sales is a Team Sport)
• The honor of presenting to my peers on Prospecting at GSKO 2020

Enterprise Accounts, Financial Services

PowerSchool

PowerSchool creates tech that makes it easier, faster, and more cost-effective for schools to find and
keep great teachers. As a former teacher, this was a purpose close to my heart.

In this role, I worked with large school districts and associations (5,000 - 50,000 employees) across
5 states. This included all stages of the sales cycle: market development, new business sales and
expansions.

• Truly partnering with the districts I served allowed me to achieve an average of 127% of my revenue goals every quarter.  
• This partnership approach also helped me do 14X what prior reps had done in the same geographic territory.
• Over 61% of my clients had never worked with us before.  Earning their trust was an honor.

Strategic Accounts

Hello Alice

Super pumped about getting my side hustle accepted into this national accelerator.  Circular Board was the Start-Up Accelerator that launched Hello Alice.

Founder - Member of Fall 2016 Founders Cohort

Haas & Wilkerson Insurance

Haas & Wilkerson is one of the nation's largest privately held insurance brokers.  I worked as a Risk Consultant partner for high attendance entertainment events across the country. 

• Created Challenger Sale strategy for National Accounts division (slide deck below)
• Sales and Business development for National Accounts division, both for-profit and nonprofit
• Strategic Sales Partnerships project team

Strategic Account Executive (Field)

My clients were all small/medium businesses and nonprofits, run by folks driven to pursue their dreams, passions and callings.  It was a thrill to develop creative solutions for their organizations.  

While the numbers alone can never tell the whole story, they do help quantify impact:
• Sales, new business development and client retention, as well as growth and operations strategies for our agency’s fastest growing unit (growth rate of 21% during my tenure)
• Created improved work processes that cleared 5 months of backlog within 8 weeks
• Introduced pilot program that increased efficiency of analysis process by 48%

Business Unit Manager - Select Accounts

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

Feel like you're trying to do everything right… but deals keep slipping, ghosting, or dragging out forever?
You’re not alone.

Enterprise sales is full of hidden traps no one warns you about:
 ❌ Deals that seem real but never close
 ❌ Discovery calls that stay surface-level
 ❌ No clear way to qualify quickly—or confidently
 ❌ “Great calls” that vanish into silence
 ❌ A cycle that feels out of your control

And somehow, you’re still expected to hit an aggressive number.
In a tough market. With no real playbook.

It’s exhausting—and it’s not your fault.


The worst part? You don’t feel in control.
You’re anxious. Burnt out.
And starting to wonder if you're even cut out for this.

But it’s not you.
You were just never taught how Enterprise sales actually works.


What if you didn’t have to figure it out the hard way?


I spent 12 years selling Enterprise deals at Salesforce, Tableau, and Outreach. I hit 47.6% win rates, broke records, and 14X’d territory expectations—but it didn’t start that way.

Early in my career, I felt stuck and scattered too. I had to teach myself how to run deals with structure, control, and confidence—because no one else was doing that kind of coaching.


Now, I teach you the strategies I wish I had sooner:
 ✅ Run Discovery that actually drives urgency
 ✅ Qualify fast—without sounding like a jerk
 ✅ Multi-thread without being annoying
 ✅ Speak the language of Executives
 ✅ Lead deals so buyers want to follow


Here’s what clients say after working together:
 👉 “Went from 2% of my number to 106%”
 👉 “Helped me close a deal with a $5B account - that 2 of my predecessors failed to close.”
 👉 “I closed the largest contract in my company’s history from prospecting to close because I implemented in real time what she taught me.“


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


Want to sell like a top performer—without waiting 10 years to figure it out?
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

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The Battle

Keith Weightman

👩🏻‍🏫 Krysten Conner

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