Kipp Bodnar - CMO, HubSpot
Kipp Bodnar joined HubSpot in 2010 as an inbound marketing strategist and increased traffic to the company blog by more than 200% and leads from it by more than 100%. Sixteen years later he is still there, the last eleven as CMO. His path ran through demand generation, first as director and then as VP, before he took over global marketing across brand, demand generation, product marketing, and content. HubSpot has grown into a customer platform worth more than $2 billion during his tenure. Writing is the other half of his work. He published The B2B Social Media Book in 2010 and has since co-authored Loop: Outlearn. Outmarket. Outgrow. with Kieran Flanagan, built around the argument that in the AI era the team running the most learning cycles beats the team with the biggest budget. Bodnar co-hosts the podcast Marketing Against the Grain and serves on the boards of Gusto, Similarweb, and Marshall University.
Cindy Zhou - CMO, Imprivata
Five exits and 16 M&A transactions, on both the buy and sell side, sit behind Cindy Zhou's two decades in cybersecurity marketing. She has built marketing organizations at publicly traded, private equity-backed, and venture-backed companies, with a specialty in go-to-market transformation. Imprivata named her CMO in March 2026. The company sells access management for healthcare and other mission-critical industries, where the goal is keeping crucial work both frictionless and secure. Zhou spends considerable energy on the profession itself. She sits on the Wall Street Journal's invitation-only CMO Council, serves on the board of the Technology Marketing Alliance, a group of more than 250 marketing leaders shaping the Washington, DC area's technology brands, and was a founding member of both CMO Huddles and the Revenue Enablement Society. She writes and speaks regularly on AI in marketing, sales, and customer experience.
Madilynn Castillo - CMO, InvoiceCloud
A pay-per-click agency in Providence, Rhode Island is where Madilynn Castillo learned the trade. At Working Planet she managed a portfolio of venture-backed B2C ecommerce and B2B SaaS accounts. FullFunnel, an outsourced sales and marketing agency in the Boston area, hired her as its first performance marketing hire, and she joined the leadership team as a director, helped grow the company 75% through direct marketing, and developed a new digital offering for B2C and B2B2C clients. Tulip Interfaces then gave her nearly eight years as CMO, reporting to the CEO and running global marketing for a composable platform used by manufacturing, pharmaceutical, and logistics companies to support frontline operations. InvoiceCloud brought her in as CMO in September 2026. The digital payments and customer engagement platform serves more than 3,250 organizations across utilities, government, and insurance, and her brief is to strengthen its market position and build a growth engine around a simple story about getting organizations paid.
Michael Welts - EVP & CMO, Wasabi Technologies
Michael Welts founded Cabletron's marketing organization in the company's early days and led its brand growth to $1.5 billion in revenue. He then ran corporate marketing at Bay Networks through a turnaround and its acquisition by Northern Telecom for more than $7 billion. Castle Networks came next, where he helped pioneer the VOIP switch category before a record-setting sale to Siemens and the formation of Unisphere. He has also been an operator. Welts served as CEO of NextChoice Systems, a pioneer in online food ordering, co-founded the safety alert app company Ping4, and co-founded Gemr, where he co-raised a $4.9 million Series A. Wasabi hired him as CMO in January 2017 to market hot cloud storage, a company on a mission to turn storage into a utility like electricity. He spent a year as CMO of Aviatrix in 2022 and 2023 while advising Wasabi's board, then returned and became EVP and CMO in December 2025. Thirty years of brand building sit behind that record.
Kris Lande - CMO, OutSystems
Trailhead was Kris Lande's proving ground. She joined Salesforce in 2012 and spent 13 years there, running product marketing for the Salesforce1 mobile launch, then developer marketing, then serving as CMO of Trailhead, the company's learning platform. Her final role was SVP of marketing and community, leading a cross-functional team of 250 people across product marketing, developer marketing, learning content, and content marketing. Advisory work followed. From 2024 she consulted for fast-growth SaaS companies on strategy, branding, positioning, and launches, with clients including Obsidian Security, Lattice, and Revmo AI. One of those clients was OutSystems, which hired her as CMO in October 2025. Twenty years in, her range covers product marketing, brand, PR, events, community building, and demand generation across both B2B SaaS and consumer engagement.
Jamie Domenici - CMO, Klaviyo
Operations came first for Jamie Domenici. She ran order processing and manufacturing procedures at OSIsoft, then global sales and marketing operations at Ingres, where she designed the lead-to-cash process from system architecture through business practices. Salesforce hired her in 2010 and kept her more than a decade, through product marketing for Data.com, Sales Cloud, and Analytics Cloud, then VP of product marketing and SMB marketing, then global SVP of customer success covering adoption, marketing, premier sales, and business development. She launched Customer Success Cloud and the Success as a Service offering. GoTo then made her CMO, where she led the rebrand from LogMeIn. Klaviyo hired her in August 2023 and she took the company through its IPO while sharpening its positioning around building the B2C CRM category. Domenici now spends her time on how the CMO role is being redrawn around AI agents, and on what it means to lead a marketing organization that has to make judgment calls faster than the agent layer can compress them.
Kelly Esten - CMO & COO, Enterprise, Toast
Kelly Esten was EnerNOC's first product marketing hire. She built the function from nothing, then redesigned the company's enterprise product offering, consolidating three disparate products and launching a new software offering that produced the best quarter for software sales in company history at 94% year-over-year growth. New value-based pricing tripled average selling price while reducing discounting. She also negotiated a strategic partnership with PwC and earned the MegaWATT Award, EnerNOC's highest honor. Then she moved to the other side of the house, taking over enterprise software sales with full revenue accountability, where her first full quarter under a restructured team delivered a 2.75X increase in new annual recurring revenue. Toast hired her in 2017 for product and partner marketing. Nine years and five promotions later she is CMO and COO of Enterprise, having served as SVP and general manager of the enterprise business along the way. Esten began her career at UBS and holds a degree in environmental science from Dartmouth and an MBA from Tuck.
Kim Salem-Jackson - EVP & CMO, Akamai
Field marketing for financial services was where Kim Salem-Jackson started at Informatica in 2009. She spent nine and a half years there, moving from principal marketing manager to director of field marketing for North America to VP of regional marketing and business development for the Americas, and finally to SVP of global marketing and business development. Akamai hired her in 2017 as global VP of marketing and corporate communications, promoted her to SVP two years later, and made her EVP and CMO in February 2021. Her remit is unusually broad, covering demand generation, brand strategy, generative engine optimization, data analytics and science, corporate communications, product marketing, field marketing, and digital. She has spent the past several years building what she calls an AI-confident organization, integrating the technology from data analytics through content creation. Salem-Jackson sits on the board of the Akamai Foundation and has been recognized as a Top CMO in Boston, one of the Top 50 Women Leaders in Software, and a member of the Global B2B CMO 100.
Jonathan Bedard - CMO, Bullhorn
Jonathan Bedard structured pharmaceutical deals before he ever ran a marketing team. At Vertex Pharmaceuticals his business development work included a $505 million secondary stock offering, a $400 million convertible debt issuance, the $375 million acquisition of ViroChem Pharma, and a $155 million securitization of future Johnson & Johnson milestone payments. He moved into strategic planning there, then spent time on business development at MassChallenge and at Tradeshift in Copenhagen. athenahealth gave him six and a half years and three jobs: chief of staff to the president of enterprise solutions, director of enterprise inside sales, and executive director of product marketing. Bullhorn hired him as SVP of product marketing in 2019 and promoted him to CMO in July 2023. His career started in GE Capital's Financial Management Program.
Stephanie Sherman - CMO, DraftKings
Stephanie Sherman was employee number 15 or thereabouts at DraftKings when she joined in 2013. Thirteen years later she runs its marketing. Her rise went from senior manager through VP and SVP before she was named CMO in January 2022, a promotion that consolidated every marketing function under her, including brand and agency campaigns, media buying, and influencer strategy. She led the company through its first Super Bowl campaign and has watched a single-product daily fantasy business become a multi-brand platform spanning sportsbook, online casino, and digital collectibles in a heavily regulated category. Vistaprint trained her first. Over nearly six years there she started as a marketing associate in Australia, ran SEO, affiliate, display, and email acquisition for the Australian and New Zealand sites while managing more than 50 partners, and finished with P&L ownership of US television and radio. Adweek has twice named Sherman one of the most powerful women in sports.
The Case for Staying Put
Read these ten records together and the striking thing is not where people came from but how long they stayed once they arrived. Toast promoted Esten five times. Akamai promoted Salem-Jackson twice before handing her the top job. Bullhorn, HubSpot, Wasabi, and DraftKings all did the same. That pattern says something about how these companies think, and something about the marketers too. Building a brand for a decade at one company is a different discipline than arriving with a playbook and executing it in eighteen months, and Boston seems to produce people willing to do the slower version.