Solving demand gen headaches ➿

Helping B2B SaaS companies build tomorrow's GTM engines. 

Former in-house marketing leader at Chili Piper, Campaign Monitor, and VP Marketing at Refine Labs. I deliver sustainable revenue growth for Series A to C companies via strategies and frameworks you won't find in a blog post. 

Wins: 
- Orchestrated $45M+ in pipeline in 18 months 
- Launched ABM programs with 3.5x lift in conversion 
- Operationalized attribution and content as revenue levers 
- Scaled new demand gen engines and rebuilt broken ones 

Are you scaling smarter? My specialties: 
• GTM Strategy & pipeline acceleration 
• ABM & demand generation 
• Paid & organic revenue alignment 
• Fractional/interim marketing leadership 
• Multi-channel campaign design 
• Full-funnel performance analysis 

I publish frameworks and templates weekly: demandloops.substack.com. 
DM to connect for GTM audits, fractional support, or advisory.

Kaylee Edmondson

Thoropass

Responsible for driving our GTM Mid-Market & Enterprise strategy and revenue growth on net-new business. Key areas of focus are ICP identification, pricing, sales motion & positioning, driving marketing efforts on brand awareness & increase of SQLs, product roadmap design, partnerships planning, channel awareness and revenue growth.

Sr. Sales Leader - Upmarket Expansion 

Thoropass is a full end-to-end compliance and security SaaS solution, driving organizations compliance program efficiencies and cost savings with quality. We have created a unique offering that emliminates the Auditor loop holes through the OrO™ Way approach. 

What is the OrO™ Way? Ask me!

Sr. Sales Leader

Pavilion

Executive Member

Secureframe

[Impacted by Reorg Layoff]

Secureframe is the leader in security compliance automation, enabling organizations to scale, build trust and stay secure with their customers in the areas of SOC 2, ISO 27001, PCI DSS, HIPAA, NIST, and more. 

Responsible for leading and overseeing the sales organization as a first / second-line level leader, obtaining net-new business and upselling current customer portfolio. Led sales across North America and EMEA, focusing on SMB, Mid-Market and Enterprise B2B software companies. 

Accomplishments 
2022
• Q2: N/A / Q3: 89% to Quota / Q4: 103% to Quota 
• Team won largest Enterprise customer to date in company history / largest ARR deal sold to date 
• Oversaw SDR team as interim Leader for 2 months - production increased in booked meetings 
• Increased team win rates from 19% to 26% in 2H of 2022 
• Grew sales team in 2022 from 7 Account Executives to 23 

2023
• Q1: 101% to Quota / Q2: 104% to Quota 
• 10 Rip & Replace competitive deals in 1H of 2023 (most in company history) 

Overall
• Took on "interim Head of Sales" for a period of 6 months 
• Developed and managed the top 2 reps in the company out of 15 
• Developed key strategies and planning on upmarket expansion in 2023, Mid-Market & Enterprise 
• Most competitive Rip & Replaces in company history 
• Implemented new sales process, such as the rollout of Command of the Message / MEDDICC company-wide

Sales Director

Datto, Inc.

World’s leading provider of cloud-based security & technology software in the areas of SaaS PSA/RMM, Unified Continuity and Networking. Overseeing the Southeast Region territory of 250+ Enterprise and Mid-Market Current Customers and New Business as a 2nd line-level leader. 

• 2nd line-lever leader responsible for the growth of Enterprise / Mid-Market  net-new logos and current customer expansion: (2) Sales Manager & (16) Indirect AE's
• 2021 Quota of $5M Net-New (100% to Quota) / $2M Expansion (99% to Quota)
• Team sold biggest RMM software deal in NA for $1.2M TCV
• Achieved/Exceeded monthly/quarterly quotas for pipeline and reoccurring revenue bookings, minimizing churn/loss and delivering on net bookings
• Provided sales/leadership Training and Coaching in the areas of net new business sales cycle, along with up-sell/cross-sell within existing business

Sr. Manager, Regional Sales

Optomi Professional Services

OPS is a full-service technology organization focused in the areas of Technology Professional Services, Domestic BPO/Outsourcing, Talent Solutions and Software. Responsible for the growth of National Enterprise Sales New/Existing business, along with mid-market sales.

• Responsible for leading (6) National Enterprise Sales Directors, along with (1) Sales Manager working with our Current Enterprise Customer base, along with developing net New Business
• Developed GTM strategy for our SaaS Workforce Management platform for new/existing customers
• Managed National Enterprise Strategic / Regional Market sales strategy
• Defined field sales metrics and developed new sales processes, along with the rollout of a consultative sales methodology (Command the Message) 
• Drove monthly account reviews within the national sales team, along with the support of our regional Mid-Market / SMB

Sr. Director of Strategic Sales

• Managed, strategized and trained in the areas of IT BPO (Business Process Outsourcing) and Human Capital Management (Staffing) within National Enterprise and Regional Market sales
• Created entire Sales Training program, new and existing hires, from ground up 
• Increased ramp-up time for new Account Executives in their first 4 months vs 7 months

Director of Sales 

Kforce Inc

As a 2nd line-level leader, I was responsible for the sales growth and management of the North Texas region, through Technology Talent Solutions, IT Outsourcing and Professional Services within Enterprise and Mid-Market sales

• Grew and managed a $37.5M P/L region, from $26M, along with two offices 
• Managed Delivery Director, (2) Market Managers, (3) Strategic Enterprise Sales Directors, along with (31) indirect reports (consisting of Recruiters, Sales Executives and back-office) 
• Trained employees, across the nation, on MEDDIC, a Consultative Sales Framework 
• Maintained top margins of 27.5% amongst 16 other offices two consecutive quarters 
• Responsible for the oversight and direction of top National Enterprise Customers; AT&T, Microsoft, NTT Data, Cisco, Toyota North America, Southwest Airlines, Allstate, Verizon, USAA, 7-Eleven, and more

Regional Sales Director

BridgePoint Technologies

Driving profitability and strategically steering all aspects of sales and operations across BridgePoint’s Information Technology Professional Services, Business Solutions/Software Development, Managed Services and SaaS Work Order / Procurement platform portfolios. 

•	Oversaw and managed company revenue of $26.5M+ across all business units - $21M+ Services / $3.8M ARR Software 
•	Grew sales from $9.5M to $14M+ in 1st year, 65% first-year growth
•	Oversaw (2) Managers, (10) Sales Executives and (6) recruiters, along with indirect reports 
•	Trained and coached consultative sales in the areas of ITO, BPO, Managed Services and Software Work Order platform solutions

Director of Sales

Aerotek

Responsible for overseeing 5 new Account Managers within the Chicagoland area within Engineering, Professional Services, and LI.

Sr. Sales Manager

Responsible for the growth of new and existing Enterprise / SMB business within Engineering and Professional Services.

•	2-time year-end sales contest winner
•	Million Dollar Club winner, driving over $1.5MM in sales profit 
•	2012 year-end total revenue of $9.5MM 
•	Consistently ranked within top 15 over a period of 2 years out of 150 producers

Sr. Account Executive

Senior Recruiter

With over 14 years of experience at the forefront of sales leadership, I excel in driving revenue growth and orchestrating successful (GTM) go-to-market strategies across diverse markets and industries. My journey has been marked by a proven ability to manage and inspire high-performing teams, including Sales Directors, Managers, Account Executives, and SDRs, both in North America and EMEA.

I specialize in crafting and executing strategies that propel companies into the Mid-Market and Enterprise space, including SMB, leveraging a blend of strategic selling methods like Command the Message, Winning by Design, MEDDICC, Gap Selling, Enterprise Sales and much more. My expertise lies not only in guiding teams towards ambitious revenue goals but also in fostering the development of sales leaders and sellers, ensuring sustained success and growth.

Throughout my career, I have designed and implemented robust sales processes that drive efficiency and effectiveness. My focus on integrating innovative methodologies with practical application has consistently resulted in enhanced performance and achievement of key business objectives. Whether leading net-new business acquisition, account management, or renewal initiatives, my approach is rooted in a deep understanding of market dynamics and a commitment to delivering exceptional results.

I am passionate about empowering teams, developing future leaders, and driving transformative change within organizations. Let's connect and explore how I can contribute to your team's success and your company's growth journey.

Solution & Industry Expertise: 
• SaaS (Software-as-a-Service) 
• Technology / Professional Services 
• SMB / Mid-Market / Enterprise 
• Series B, C and D venture backed / Pre/Post IPO 
• Security, Cybersecurity, Compliance, GRC, Human Capital (HCM), BCDR, Sales, Infrastructure, Application Development 

Skills & Experience: 
• GTM Leadership - Enterprise / Mid-Market / SMB Sales 
• Net-new / Expansion & Account Management / Renewal 
• Talent Development & Management of SDR's, Account Executives, Account Managers, Sales Managers and Directors
• GTM Sales Strategy, Sales Ops, Product Development and Marketing  
• Organizational Change Management (OCM)
• Sales Systems and Processes Design / Implementation
• Sales/Operational Strategic Planning & Forecasting 

https://www.saasrampmedia.com/podcasts/the-difference-between-sales-and-service/

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The Battle

Kaylee Edmondson

Jon Mathews

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