Stuart Kaplan

I am a dynamic, eneergetic leader who has built, managed, and grown high-performing SaaS sales teams with over 20 years of experience in multiple industries. I’ve created successful commercial go-to-market plans to leverage existing relationships and pursue new customers in verticalized software.

• Drove $24m+ ARR growth, exceeding revenue plans at multiple companies
• Created GTM plans for value creation in sales & marketing
• Improved efficiencies, developed standardized processes, and scaled sales teams at numerous companies
• Built new logo and account management teams to drive pipeline expansion, upsell/cross-sell, & new business
• Dynamic, accountable, hands-on leader with exceptional communication skills

Executive Business Leader, Sales & Go-To-Market Expert, Board Member – Driving Exceptional 

• Track Record of SaaS Revenue Generation

Delivered $24m+ of annual net new recurring revenue for multiple SaaS companies, overachieving ARR bookings goals. Successful $1.4B acquisition by GI Partners in 2019 and a $2.7B acquisition by Bain/Vista in 2016.

• Outstanding Communicator and Relationship-Builder

Develops trust-based open relationships across the organization with listening rigor, structure, and empathy. Enthusiastically delivers information to align with internal priorities, calls-to-action, and process standardization.  Creates and implements unified go-to-market strategies. Builds lifetime relationships with customers

•  Strong People and Team Developer 

Passionate about coaching, mentoring, inspiring, and leading teams by example. Ability to unify teams, cultures, and companies through dynamic leadership, energetic and contagious optimism, and making work fun! Successfully scaled multiple sales organizations.

PROFESSIONAL EXPERIENCE

PAYA                                                                                                                                                                                    2022

Recruited to grow the Insurance vertical including M&A and rapidly scale a direct sales force. Paya is a leading provider of integrated payment and frictionless commerce solutions.

Senior Vice President, Sales                                                                                                           

• Drove total insurance revenue growth over 33% YoY through partner engagement
• Developed $7m+ of new business and new logo pipeline, both partner and direct opportunities
• Increased new revenue growth by 76% YoY, implementing account planning and new go-to-market strategy

INSURITY                                                                                                                                                                     2019 - 2021

Hired to lead, manage, and grow the field sales team including sales operations and business development. Insurity is a leader in the policy administration, analytics, and data software market for carriers and MGAs.

Vice President, Sales                                                                                                                     

• Drove 25m+ of net new recurring revenue in 2019 & 2020, overachieving bookings goals. This was a 17% improvement on average YoY. Successful acquisition by GI Partners in 2019
• Created and implemented a new logo sales model resulting in 19 new logos, an increase of 238% YoY
• Achieved new business booking growth of 34% YoY from 2019-2020
• Increased recurring revenue pipeline by 183% from 2019 to 2021, resulting in a $72m pipeline
• Established and rolled out sales methodologies and tools to drive consistent, repeatable, and predictable forecasting, in 7 out of 8 quarters
• Successfully integrated 5 acquisitions in 2020 into the Insurity sales process and increased pipeline velocity

VERTAFORE                                                                                                                                                             2008 - 2019

Recruited to sell into large, strategic accounts. Promoted to Director and then Vice President, managing, scaling, and growing the largest segment of Vertafore. Vertafore is a leader in the insurance software, analytics, and data market for independent agencies, MGAs, and carriers.

Vice President, Strategic Accounts                                                                                                 

• Created and delivered initiatives to drive 31% of net new bookings ($24m/yr.), over-achieving revenue

and performance goals 

• Increased YoY recurring bookings by 11% in 2017 and 2018
• Created and managed client executive programs focused on leadership, development, and industry education
• Increased sales team by 283% to drive future growth and recurring revenue expansion
• Coached, developed, and led a team of 17 senior sales executives as well as specialists and solutions consultants

Director, Strategic Accounts (Player/Coach), Senior Sales Executive                                             

• #1 Sales Executive (new revenue production) from 2010-2015
• Closed an average of $5m+ in new business per annum in strategic national accounts
• Managed complex client relationships resulting in accelerating client growth, operational process improvements, and increase efficiencies

THE ADVISORY COUNCIL (TAC)                                                                                                                      2007 - 2008

Hired on the ELT to stabilize and grow revenue. TAC is a boutique advisory services firm providing custom IT & business research, consulting, and leadership services. 

Executive Vice President, Global Sales                                                                                                    

• Increased client retention by 240% by implementing a structured program and redesigning sales processes
• Built and managed a strategy practice, which led to a 316% YoY increase in consulting revenue
• Developed a new leadership services program, generating over $100k in new account revenues
• Recruited and managed subject matter experts resulting in a 54% increase in on-demand experts
• Managed and improved sales, delivery, and customer service teams

GARTNER                                                                                                                                                                                                1999 - 2007

Joined as a Producer to manage and grow F500 accounts, including technology, manufacturing, consulting, retail, and financial services. Gartner is the world’s leading information technology research and advisory firm.

Global Account Manager                                                                                                    

• Top 1% in the world (over 750 sales executives)
• Increased global account revenues by over 200%, closing large consulting and benchmarking deals averaging $1.2 million per year
• Opened new strategic accounts working with C-level executives and grew multi-national relationships

COMPUCOM SYSTEMS (FORMERLY CIC & COPLEY SYSTEMS)                                                                                           1992 - 1999

Hired as a rep, and promoted to run New England, then the East Coast. CompuCom is a systems integrator.

Regional Director/ Branch Manager/ Senior Account Executive

• Increased branch revenue by over 275% in four years to over $55 million
• Exceeded monthly, quarterly, and yearly quotas by over 185%
• Built and managed the largest branch in the company (revenue and gross profit)  

NCR CORPORATION                                                                                                                                                                           1990 - 1992

Account Manager                                                                                                                

Responsible for penetrating and managing Fortune 500 clients in manufacturing.

• Managed and coordinated enterprise selling activities to CIO and VP levels of Fortune 500 companies resulting in three promotions in 18 months

BA, Marketing

University of Massachusetts, Amherst