👩🏻‍🏫 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

Member

Lightstyle of Orlando and Tampa Bay

My journey is uniquely full-circle: I once was a valued customer of Lightstyle, and now I return as its leader. This experience gives me a profound understanding of what drives customer satisfaction and loyalty. With this insight, I am committed to delivering exceptional service and innovative solutions that illuminate spaces and inspire lifestyles across Central Florida.

President

MVP-Results - Creating MVPs at every level

☛ Led C-Suite in talent optimization using science and data

❑ Coached entrepreneurs to build strong teams and improve communication
❑ Designed Go-To-Market and value-based sales strategies for businesses

VP - Strategy and Development

Maple Street, Inc.

☛ Led re-launch of Contract Lifecycle Management/Risk/Compliance SaaS BPM platform for Financial Institutions, increasing close ratios from 30% to 60%.

❑ Exceeded YOY growth targets by 121% in first six months.
❑ Revamped Marketing Messaging, attracting C-Suite audience and improving lead generation by 17%.

Chief Revenue Officer - SaaS 

CORT Events

☛ Led regional sales team to achieve #1 national ranking in 2019 and 2020, exceeding goals by 107%.

❑ Increased profit margins by 40% and expanded partnerships by 300% in Hospitality and Event Production.
❑ Delivered top-line growth of 19% in 2019 and on target for 22% increase in 2020.

Regional Director of Sales

Ricoh Americas Corporation

☛ Transformed commercial sales and support teams to focus on digital information process and cloud services, leading to a 52% team performance improvement in 2016.

❑ Implemented process improvement services across various departments such as Human Capital, Customer Experience, Finance, and Supply Chain.
❑ Inspired teams at Ricoh Americas Corporation to share and achieve the vision of launching a new SaaS/AI Platform, growing Monthly Recurring Revenue to $10M in 2 years.

Sales Manager - Digital Transformation with SaaS

Earlier Accomplishments

☛ VOIANCE LANGUAGE SERVICES - Led company market presence from #30 to #2 in 3 years – generating a record $50M Monthly Recurring Revenue per year

☛ ADP CLAIMS SERVICES GROUP - Pioneered presence in Puerto Rico, Established 8% market share from $0 to $36M ARR in 16 months 

☛ XO COMMUNICATIONS – Led Branch from Worst to First - #33 to #1, Remained #1 for 13 straight months as General Manager 	 

☛ EPIK - Early-Stage Start-up, Pre-Revenue/Pre-Product from $0 TO $300M ARR in 1 year as Director - IP Services 	

☛ TW TELECOM - Early-Stage Start-Up, Pre-Revenue/Pre-Product from $0 TO $100M ARR in 5 years as Regional Data Manager

Previous Experience for Pre-Revenue Start-up and Market Turn-Around

Lead Teams to achieve more than they dreamt possible ◦ Empower Clients to succeed in ways they could not envision ◦ Sales Leadership ◦ Revenue Growth ◦ Strategy ◦ Team Development ◦ Transformation ◦ Culture Creator

As President of Lightstyle of Orlando and Tampa Bay, I lead with vision, strategy, and a passion for empowering teams to achieve extraordinary results. With a proven track record of scaling businesses, driving revenue growth, and fostering innovation, I thrive at the intersection of leadership and market disruption.

Throughout my career, I have guided four early-stage startups to $300M ARR, revitalized three mature companies through strategic turnarounds, and launched four successful products and divisions—all while exceeding revenue targets. My expertise lies in building high-performing teams, creating scalable processes, and navigating complex challenges to deliver transformative results.

At Lightstyle, I am committed to advancing our legacy as Central Florida's premier lighting leader by combining industry expertise with a customer-first philosophy. By aligning cutting-edge design with operational excellence, we aim to illuminate spaces and inspire lifestyles across Orlando and Tampa Bay.

Outside the boardroom, I am an avid reader, Harley Softail rider, scuba diver, and coffee enthusiast. I also enjoy exploring wine and cheese pairings while connecting with people who share a passion for creativity and innovation.

Core Competencies:

Strategic Leadership & Revenue Growth

Team Building & Talent Development

Market Disruption & Scaling Operations

Customer Experience Optimization

SaaS, AI, & Tech Solutions Expertise

P&L Management & Budgeting

Industries Served:
Lighting & Design | SaaS | FinTech | AI | Manufacturing | BPO/BPM

Why Connect With Me?
Ask me why a CEO once called me the "Mary Poppins of Sales Leadership." Whether it's building teams or transforming companies, I bring the tools to create magic in any business environment.

taplio

The Battle

👩🏻‍🏫 Krysten Conner

Tricia Holliday, MBA

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