The Top 25 Software Sales Executives of 2023

The Software Report is pleased to announce The Top 25 Software Sales Executives of 2023. These awardees represent some of the most achieved professionals when it comes to harnessing effective sales strategies and leading high-performing teams. Overall, the men and women who made this year's list are not only responsible for selling a company's products and services, but are also instrumental when it comes to building customer relationships. We recognize the outstanding achievements of those individuals who enable their companies to continue thriving, innovating, and impacting society for the better.

Sales leaders were nominated based on their demonstrated career commitment to the software industry and their ability to consistently drive business growth and customer satisfaction. Awardees include Ron Gabrisko, Chief Revenue Officer at Databricks, who has built and led the Databricks’ sales team from the early stages to a $38 billion market valuation; Intellect's VP of Sales, Peter Culter, a seasoned veteran with nearly 40 years of experience leading sales teams; and Robert Brooks, a Founding Team member and VP of Revenue at Lambda, a deep learning infrastructure company that serves the likes of Sony, Raytheon, MIT, Harvard, and the Department of Defense.

As software sales continue to explode as one of the fastest-growing career paths in tech, the deep expertise of these awardees becomes all the more valuable. Please join us in celebrating the achievements of The Top 25 Software Sales Executives of 2023.


1. Ron Gabrisko
Company: Databricks
Title: Chief Revenue Officer

At Databricks, Ron Gabrisko is the Chief Revenue Officer. In this role, he is responsible for managing the worldwide sales organization and go-to-market strategy for the $38 billion software giant. Earlier, Gabrisko built and led the Databricks’ sales team from the early stage to a successful IPO. With origins in academia and the open source community, Databricks was founded in 2013 by the original creators of Apache Spark™, Delta Lake, and MLflow. As the world’s first and only lakehouse platform in the cloud, Databricks combines the best of data warehouses and data lakes to offer an open and unified platform for data and AI.

Most recently, Gabrisko served as SVP of sales for Axway Software. During his leadership there, he was instrumental in developing the sales team: building it up from its nascent stages, and later guiding it through the company’s successful IPO. Prior to Axway, he was responsible for sales, business development, and marketing at Cyclone, a Trinity Ventures-backed company. Gabrisko holds an MBA and a Masters in Engineering from Stanford University. He also has a Bachelor of Science in mechanical engineering from Purdue University.


2. Sean Walters
Company: Datadog
Title: Chief Revenue Officer

Sean Walters, the Chief Revenue Officer at Datadog, has an impressive track record of over two decades in enterprise software sales. Since joining the New York City-based software company in 2018, Walters has demonstrated exceptional achievements and strong leadership skills. Prior to his CRO role, he served as Datadog’s SVP of global enterprise sales; and VP of sales for the company’s Americas and EMEA businesses.

Throughout his career, Walters has established himself as a trusted industry expert by holding key sales leadership roles at renowned technology companies, including Medallia, BMC Software, and IBM. His profound understanding of the sales landscape and astute business acumen has consistently made him a valuable asset in each organization he has been a part of. Walters’ educational background includes a Bachelor of Science in marketing from Rowan University, which equipped him with a solid foundation in strategic marketing principles and a nuanced understanding of consumer behavior.


3. Sean Nappo
Company: Aptean
Title: General Manager and Senior Vice President of Sales, Americas

Sean Nappo is the General Manager and Senior Vice President of Sales for the Americas process business unit at Aptean. In this role, he oversees overall operations and business success for the group; and is dedicated to building valuable, successful, and lasting partnerships with customers. Aptean is one of the world’s leading providers of purpose-built, industry-specific software that helps manufacturers and distributors effectively run and grow their businesses. While the company is headquartered in Alpharetta, Georgia, it also maintains offices in North America, Europe, and Asia-Pacific.

Nappo has over 14 years of experience selling and supporting SaaS enterprise software across the manufacturing and education industries. He joined his current company in 2020 as VP of sales for North America. Before Aptean, Nappo held various sales leadership roles, establishing a consistent track record as a top leader driving his teams to exceed quota targets, generate revenue growth, and build business profitability. Most recently, he served as regional vice president for Ellucian, a SaaS-enabled ecosystem of open and flexible technologies. Nappo holds a Bachelor of Science in economics from College of the Holy Cross, where he also played Division I hockey.


4. Jonas Samsioe
Company: Kaseya
Title: Vice President, and Head of Sales and Revenue Operations

Jonas Samsioe began his professional career 12 years ago. He currently serves as the Vice President and Head of Sales and Revenue Operations at Kaseya, a leading provider of unified IT management and security software for managed service providers and small to medium-sized businesses. With a customer-centric approach, Kaseya delivers top-tier technologies for efficient IT management, security, and backup. Kaseya offers a comprehensive range of IT management solutions, including renowned brands such as Kaseya, IT Glue, RapidFire Tools, Spanning Cloud Apps, ID Agent, Vonahi, audIT, Graphus, RocketCyber, TruMethods, and Unitrends.

In 2011, Samsioe started to cut his teeth as a director of sales operations for global merchant services at American Express. He later joined Dun & Bradstreet; and subsequently achieved the position of principal at Blue Square Partners, his most recent role prior to joining Kaseya. Samsioe holds an MBA from INSEAD and a Bachelor of Science in finance and information systems from NYU Stern School of Business.


5. Craig Vario
Company: ThousandEyes
Title: Senior Vice President of Global Channel Sales

Craig Vario is the Senior Vice President of Global Channel Sales for ThousandEyes, which is now part of Cisco’s Enterprise Networking and Cloud Business unit. Vario is an accomplished business leader with deep experience in enterprise software and channel sales. He has more than 20 years of technology leadership experience, including 15 years in the service provider market. ThousandEyes delivers visibility into digital experiences delivered over the Internet. The world’s largest companies rely on its platform, collective intelligence, and smart monitoring agents to get a real-time map of how customers and employees reach and experience critical apps and services across traditional, SD-WAN, Internet, and cloud provider networks.

Before joining ThousandEyes, Vario held multiple different leadership roles at CA Technologies, which was acquired by Broadcom. During his lengthy 17+ year tenure at CA Technologies, he was responsible for building and managing a complete go-to-market strategy for the company’s largest and strategic global partners. Vario earned a master's in business management from Dowling College and a bachelor’s in business administration from Hartwick College.


6. Tim Rafferty
Company: 15Five
Title: Head of Sales

Tim Rafferty is currently the Head of Sales at 15Five. Positioned as a comprehensive performance management organization, 15Five empowers HR teams with a unified platform solution, fostering improved managerial efficacy, enhanced performance and engagement, and heightened employee retention rates. By seamlessly integrating user-friendly software with personalized coaching, managerial training, and a vibrant professional community, 15Five's methodology equips HR leaders with the necessary tools to effectively realize their strategic human capital objectives.

Rafferty joined the 15Five team more than 6 years ago, holding positions of increasing responsibility at the company. Before 15Five, he spent nearly 3 years as an associate at Pavilion. Earlier, Rafferty began his professional career as a sales development representative at Qualtrics in 2015. He received two degrees from the University of Limerick. He holds a master's in international management and global business, as well as an undergraduate degree in food science and health.


7. Ryan Maggio
Company: Xactly
Title: Vice President of North America Sales

Ryan Maggio is the Vice President of North America Sales at Xactly. Launched in 2005, Xactly is a company founded by a sales leader and is committed to empowering salespeople worldwide. Its AI-powered intelligent revenue platform equips revenue operations teams with critical data for agile strategizing, purposeful inspiration, and confident forecasting.

With over 14 years of experience, Maggio has spent his entire career at Xactly. He first came on board n 2010 as a business analyst. During his early years with the company, he is credited with closing ​2000+​ sales compensation support cases with a​ 96%​ customer satisfaction rating. Later, he went on to serve in such positions as lead for the solutions consultant team and director of enterprise sales, among other roles. Over his career, he has become an expert in compensation, forecasting, and intelligent revenue, demonstrating unwavering dedication to serving clients. Maggio holds a Bachelor of Science in business marketing from San Jose State University.


8. Steve Travaglini
Company: LinkSquares
Title: Chief Revenue Officer

Steve Travaglini is the Chief Revenue Officer at LinkSquares, where he is responsible for driving sales, customer success, and business development strategies at the company. He assumed the role in 2021 after joining as the VP of sales. LinkSquares is renowned for its AI-powered contract management platform, which is highly favored by legal teams seeking to expedite business progress. The company equips customers with comprehensive tools for enhancing contract composition, facilitating swift contract execution, conducting thorough contract analysis, and promoting seamless collaboration within their teams.

Prior to his tenure at LinkSquares, Travaglini held the position of head of sales at Onshape, a cloud-based CAD startup. Additionally, he served as the senior sales team lead at Datto, Inc. Travaglini obtained his undergraduate degree from Assumption University.


9. Sue Nolin
Company: Wasabi Technologies
Title: Vice President of North America Sales

Sue Nolin started her professional journey 27 years ago. Today she is the Vice President of North America Sales at Wasabi Technologies, a company that specializes in hot cloud storage: offering a swift, cost-effective, and dependable cloud storage solution. In contrast to Amazon, which tends to restrict businesses with its costly storage options and undesirable vendor lock-in, Wasabi provides fast, affordable, and reliable cloud storage. Consequently, customers enjoy a pricing advantage of being only 1/5th the cost of Amazon S3, along with superior speed compared to competitors, and without any additional charges for egress or API requests.

Nolin's career began in 1996 as a sales support manager at CSI Netlink. She subsequently joined Altiga Networks before progressing to the roles of sales operations director and SFDC administrator at Datawatch Corporation, her most recent position prior to joining Wasabi. Nolin received her Bachelor of Arts in English from the Massachusetts College of Liberal Arts.


10. Mark Paske
Company: Fortra
Title: Global Vice President of Sales

Mark Paske is the Global Vice President of Sales for Fortra's Cybersecurity, Intelligence, and Automation business. Paske brings a wealth of experience in leading dynamic SaaS and software sales organizations. He is known for being a customer-centric executive who focuses on solving complex problems by emphasizing customer value and fostering strong channel partner relationships.

With over 27 years in sales and sales leadership, Paske has held executive positions at three SaaS companies, most recently serving as the CRO at Balto, a leader in conversational AI. Paske previously worked at virtualization and cloud automation powerhouse VMware for 14 years, where he held roles such as VP for VMware's synergy acceleration team in the Americas; and VP of sales for the Eastern region in the U.S. Paske is a graduate of Colgate University and has been involved in coaching youth sports, running mentorship programs for his alma mater, and serving on various alumni boards. He is currently the Co-President of the Colgate University Maroon Council. Paske is also a consistent supporter and sponsor of the Interfaith Food Pantry in Morris County, New Jersey.


11. Steve Terp
Company: Appspace
Title: Chief Revenue Officer

Steve Terp is the Chief Revenue Officer of Appspace, where he leads the company's efforts to empower enterprises in creating superior workplace environments through user-friendly communication tools and efficient space management solutions. Appspace operates across the United States, United Kingdom, United Arab Emirates, and Malaysia, providing comprehensive global assistance to its clients. By facilitating workplace modernization, Appspace helps companies optimize their overall workplace experience.

With more than three decades of extensive professional experience, Terp began his career in 1991. Prior to joining Appspace, he served as the chief sales officer at Revenue Analytics, Inc., and previously held the position of president at Concerto Cloud Services. Earlier in his career, he excelled as a sales manager at National Data Products. In 1987, Terp earned a Bachelor of Science in marketing from the University of Florida.


12. Timothy Grocki
Company: Applied Intuition
Title: Head of Strategic Sales

Timothy Grocki is the Global Head of Strategic Sales at Applied Intuition. The company’s mission is to accelerate the world’s adoption of safe and intelligent machines. Applied Intuition provides software solutions to safely develop, test, and deploy autonomous systems at scale. Prior to his current position, Grocki served as the global accounts manager for automotive at Hortonworks, contributing to the company's remarkable achievement of reaching $100 million in revenue at an unprecedented pace; and successfully executing an initial public offering.

Additionally, Grocki held the position of key account director at Oracle, where he showcased his expertise in managing key accounts. Before that, he served as an account executive for the open source software business at Novell. Before venturing into sales and strategic roles, Grocki gained valuable experience as an advanced systems engineer at Electronic Data Systems. Grocki graduated from Wayne State University with an undergraduate degree in business administration.


13. Pedro Diaz Ochagavia
Company: Cloud Software Group
Title: Head of Worldwide Sales

Pedro Diaz Ochagavia has been the Head of Worldwide Sales at Cloud Software Group for the past two decades. Cloud Software Group is renowned for its expertise in data, automation, insight, and collaboration– empowering customers to maximize their software franchises. Ochagavia's career began in 2003 as an inside sales professional at Hewlett Packard Enterprise. He later joined BMC Software as a west area sales director.

Ochagavia holds a master's in information security from Universidad Politécnica de Madrid; a master's in engineering, specializing in information technology and computer sciences; and an undergraduate degree in management information systems from Universidad Pontificia Comillas.


14. Dave Kranowitz
Company: Grafana Labs
Title: Vice President of Worldwide Sales

Dave Kranowitz, the Vice President of Worldwide Sales for Grafana labs, has built and scaled numerous high-performing teams throughout his 25-year career in the enterprise technology industry. He joined Grafana in October 2019 to run global sales, making him responsible for driving scale, revenue growth, and the channel ecosystem worldwide.

Prior to going to Grafana, Kranowitz ran the enterprise sales team for Turbonomic across North America. Over his 5 years at Turbonomic, the company grew from $13M to >$100M+ in revenue; and transformed from a SMB-focused velocity motion to a true enterprise selling motion. Turbonomic was acquired for $2 billion in 2021. Previously, Kranowitz was part of the founding sales team at dynaTrace. There, he started as an individual contributor, then was promoted to a first line manager, and eventually ran the company's Eastern business. As the company grew in scale, Kranowitz was vital in the development of many of the sales processes that helped lead the company to an acquisition in 2011. Kranowitz earned his undergraduate degree from Connecticut College.


15. Maryclare Sweeney
Title: Senior Director of Sales

Maryclare Sweeney serves as the Senior Director of Sales at SEVENROOMS, a fully-integrated, data-driven guest experience platform catering to a wide range of hospitality operators. This comprehensive platform caters to a diverse range of hospitality operators, including neighborhood restaurants, bars, and international groups. To date, Sweeney has been with her company for more than 5 years. She started at SEVENROOMS as an account executive, and has steadily climbed the company ranks, holding numerous leadership positions in sales.

Commencing her career in 2007, Sweeney previously served as an enterprise account executive at Global Knowledge, a provider of IT and technology training. Subsequently, she was a senior account manager at Cyanna Education Services. Earlier in her journey, Sweeney served as a director of sales at the Institute for Integrative Nutrition. Sweeney earned her Bachelor of Arts from Goddard College.


16. Phil Bohn
Company: Mediavine
Title: SVP of Sales and Revenue

Senior Vice President of Sales and Revenue at Mediavine, Phil Bohn has been with his company for more than 5 years. Mediavine specializes in full-service ad management, offering display ad optimization, video monetization, and sponsored influencer marketing solutions for original content creators. Launched in 2004, the company was founded by content creators, for content creators. Its mission is to provide readers with the best possible user experience and clients with maximum earnings, all with full transparency.

Bohn's professional journey began in 2008 as an account executive in the outdoor division of Gorilla Nation Media. He then transitioned to Arizona Foothills Magazine, gaining valuable experience in the magazine publishing industry. Prior to joining Mediavine, Bohn held the position of vice president of programmatic sales at SheKnows Media. In 1999, Bohn received a Bachelor of Arts from Arizona State University.


17. Mason Miles
Company: CommandLink
Title: Executive Vice President of Sales

At CommandLink, Mason Miles is the Senior Vice President of Sales. In this role, Miles leads a dynamic and high-performing team, overseeing strategic initiatives to ensure that the organization delivers optimal solutions tailored to meet the unique requirements of its customers. CommandLink, which was founded in 2012, delivers superior software defined network and communication infrastructure solutions by leveraging our proprietary software platform.

Prior to joining CommandLink, Miles held an executive leadership position at Fusion Connect, a publicly-held telecommunications company with a focus on providing managed cloud networking and communications to distributed enterprises. During his tenure there, Miles's team achieved triple-digit revenue growth by offering complex solutions to large enterprise businesses, including notable engagements with prominent retail, restaurant, medical, financial, and technology corporations. Before Fusion, Miles also held an executive leadership position at MegaPath, a well-established managed network and telecommunications provider specializing in solutions for multi-location businesses. He has also worked closely with Jason Ness, the current CEO of CommandLink, during their time at GTT Communications, a multinational leader in creating international networks, and Telnes Inc., a customer-experience-managed web and engineering enterprise.


18. Yessica Cartajena
Company: Microsoft
Title: Executive Director of Global Enterprise Sales

Yessica Cartajena is the Executive Director of Global Enterprise Sales at Microsoft. She joined the company in 2018 as the digital transformation director. Microsoft, founded in 1975, aims to enable people and businesses worldwide through transformative technology. The company focuses on developing and marketing software, services, and hardware devices. Operating globally, the software juggernaut has offices in over 100 countries, revolutionizing how people navigate the digital world.

An industry veteran, Cartajena has more than 20 years of experience in business development, digital transformation programs, innovation, and go-to-market execution. Previously, she worked as a regional offering manager at IBM, where she was responsible for the company’s hybrid cloud portfolio in South America and Mexico. She’s also served as a managing solution architect at Dimension Data. Earlier in her career, she was a project manager at Corfo. Cartajena is a member of the World Bank Advisory Panel, representing the Chilean technology industry.

Cartajena holds an MBA from Pontificia Universidad Católica de Valparaíso; and an undergraduate degree in electronic engineering, computers, and telecommunication from Universidad Tecnica Federico Santa Maria.


19. Rex Galbraith
Company: Consensus
Title Chief Revenue Officer

Rex Galbraith is currently the Chief Revenue Officer at Consensus. Founded in 2103, and now with over $139 million in the bank, Consensus is a SaaS company that provides a platform for interactive video demos. Presales and technical sales teams automate repetitive product demos, which allows them to reallocate that time to higher value activities. Buyers get a better experience— one that guides them with digital, interactive and on-demand video demos.

Prior to joining the company, Galbraith was the director of sales at HireVue and the regional sales manager at Global Access. During his time there, he crushed the company’s sales quota of $1.5 Million by 306% in 2012 ($4.6 million). Galbraith also acquired 12 new clients in the first year, exceeding the entire company's previous two years of 8. Furthermore, the sales leader drafted, negotiated, and closed 36 contracts with 19 executive teams of new clients. Before that, Galbraith also served as the director of sales at Yoli and InfoTrax Systems. In addition, he was the owner of Printing Ninja. He holds two degrees, including a Bachelor of Business Administration from Brigham Young University, and another undergraduate degree from Utah Valley University.


20. Simon Lapeyry
Company: Intrinsic
Title: Head of Business Development and Sales

Simon Lapeyry is the Head of Business Development and Sales at Intrinsic, an Alphabet company specializing in the development of a software platform for intelligent robotics. Intrinsic's mission is to expand the accessibility and usability of industrial robotics to a wide range of businesses, entrepreneurs, and developers.

Prior to his current role, Lapeyry held the position of VP of growth and revenues at Vicarious, a leading provider of next-generation artificial intelligence solutions for robotics applications. At Vicarious, he led strategy, business development, marketing, and sales as the company scaled-up. Additionally, he has served as a consultant at The Boston Consulting Group, where he advised technology and industrial companies on operations and commercialization. Lapeyry holds a Master of Science in mathematics from Harvard University, where he specialized in statistics and optimization. He also received a Master of Engineering from Ecole Centrale Paris.


21. Robert Brooks
Company: Lambda
Title: Founding Team, and Vice President of Revenue

Robert Brooks is a Founding Team member and Vice President of Revenue at Lambda. With headquarters in San Francisco, California, Lambda is firmly dedicated to accelerating human progress through its provision of advanced computational solutions. The company specializes in the development of cutting-edge GPU workstations and servers, making significant contributions to empower engineers and researchers at the forefront of pushing the boundaries of human knowledge. Its clientele list includes such big players as Sony, Disney Research, Pfizer, Raytheon, MIT, Harvard, and the Department of Defense.

Brooks has been with Lambda since October 2018. Previously, he served as the head of sales at Tempo Automation. Before that, , he was sales team lead at Stack Overflow; and a registered stock broker at Charles Schwab, where he first began his career. In 2010, Brooks earned his Bachelor of Arts from Ohio University.


22. Josh Kalmus
Company: PERSUIT®
Title: Vice President of Sales, North America

Josh Kalmus is the Vice President of North American Sales at PERSUIT®, a legal technology platform revolutionizing outside counsel engagements. Founded in 2016, PERSUIT® is a SaaS company that helps Fortune 500 in-house legal teams competitively source legal work from panel firms, obtaining true market pricing. It sets the new standard for large corporate enterprises, offering centralized, streamlined, automated, and data-driven engagement.

Previously, Kalmus served as a sales and consulting manager at Exceed Global, a consulting services organization; and advisor and head of sales at Leash It Group, a technology start-up. Earlier in his career, Kalmus was a commercial lawyer at Macpherson Kelley. Kalmus uses his legal, tech, and commercial experience to identify opportunities in the market and deliver strategic direction and outcomes. He has a particular passion for working with Fortune 500 companies to leverage technology to enable more timely and informed data-driven decision making, automate manual workflows, and provide centralized, streamlined, and scalable processes. Kalmus holds a Bachelor of Laws (with honors) and a Bachelor of Arts (majoring in Chinese language) from Monash University. He is admitted to practice as a solicitor in both the State of Victoria and the Federal Jurisdiction of Australia; and is a member of the Law Institute of Victoria.


23. Peter Cutler
Company: Intellect
Title: Vice President of Sales

Since 2018, Peter Cutler has been the Vice President of Sales at Intellect, a leading provider of highly configurable QMS and no-code platform software that enables organizations to accelerate compliance, adaptability, and productivity. Hundreds of customers trust Intellect in a wide variety of industries, including manufacturing, labs, pharmaceuticals, government, aerospace, cannabis, financial services, healthcare, and many other industries.

With nearly 40 years of experience leading sales teams, Culter brings a wide range of experience to Intellect. Prior to joining the company, he served as VP of sales at Instant InfoSystems; and SVP of global sales at CrossBorder Solutions. Earlier in his career, he served as VP of sales at Thomson Reuters. Cutler holds a bachelor’s in political science and history from Boston University.


24. Scott Ciabattari
Company: Appvance
Title: Senior Director of Sales

Scott Ciabattari is the Senior Director of Sales at Appvance, a leading provider in the AI-driven autonomous test generation. Appvance's premier product, Appvance IQ, is the world's only autonomous test system that finds bugs on its own. It helps enterprises improve application quality, performance, and security while transforming testing team efficiency. Headquartered in Santa Clara, California, Appvance has offices in Costa Rica and India.

Ciabattari started his career in 1990 at Oracle Corporation as a marketing and sales professional. He later worked at Pure Software and rose to the position of strategic partnerships manager of enterprise at Google before joining Appvance. Ciabattari graduated from the University of California, Berkeley.


25. Anthony Mesa
Company: ViewLift
Title: Vice President of Sales

With nearly two decades’ worth of experience, Anthony Mesa serves as the Vice President of Sales at ViewLift, a prominent full-service digital content distribution platform. ViewLift specializes in empowering various entities such as media companies, sports leagues, and teams, broadcasters, and others – enabling them to effectively monetize their content through native branded applications on major over-the-top (OTT) devices, including web, mobile, TV-connected devices, Smart TVs, and gaming consoles.

Anthony Mesa's prior experience includes being director of sales at Zype, as well as a senior business development role at Verizon. Prior to Verizon, he spent several years at Limelight Networks, where he closed lucrative deals with Alloy Media, NASA, InTouch Ministries, Tastytrade, and other major players in various niches. Earlier in his professional journey, he served as a counselor at Apollo Group, Inc.