The Smart Business Dealmakers Dealmaker of the Year Awards recognize exceptional individuals who are shaping the landscape of business and innovation in Boston.
In addition, The Boston Dealmakers Hall of Fame recognized a class of dealmakers that has made an often-groundbreaking impact on their organizations, industries and the region over the course of decades in business.
We celebrated the accomplishments of the 2025 class of winners on March 20 at the Boston Smart Business Dealmakers Conference. Together, they provide a strong picture of the Boston business community.
Dealmaker Of The Year Honorees
Brett L’Esperance, CEO of Dauntless Air. Dauntless Air operates the largest North American fleet of specialized, amphibious aerial firefighting airplanes called the “Fireboss,” which support wildfire response across North America to assist state and federal agencies in their battle against wildfire. Since acquiring the business in 2017, Brett has grown the flight from nine Fire Bosses to 20 and dramatically expanded the company’s service geography and customer base. In April 2024, Brett expanded the fleet through the acquisition of a competitor’s planes and refinanced existing debt via a Farm Credit system backed term loan.
Marc Fontaine, Operating Partner, Anvil Capital. In January 2025, Anvil Capital completed the successful sale of Air Temp to PremiStar, a leading national HVAC and building automation services provider. During Anvil Capital’s ownership, Air Temp executed four add-on acquisitions, increasing revenues by 6.5x and EBITDA by 8.5x. Marc Fontaine’s strategic oversight was instrumental in scaling operations and optimizing value, positioning Air Temp as a premier player in its sector.
Nan-Wei Gong, FIGURE8 Inc. Nan-Wei has an amazing story, coming to the U.S. for grad school, stayed after her first venture won the MIT 100K competition and was acquired by Google. Nan-Wei has a passion for making solutions accessible to the masses and expanding physical therapy from an elite market to the masses. FIGUR8 is the market leader in measuring musculoskeletal health and tracking injury recovery. Through its innovative, FDA-registered bioMotion Assessment Platform and clinical AI note-taking tool, MovementMemo, FIGUR8 empowers payers, providers and patients with valuable decision-making insights at every stage of the recovery process. A venture-backed MIT spinoff, FIGUR8 has raised over $43 million in venture funding, including a recent $28 million Series A-1 round led by First Spark Ventures, Phoenix Venture Partners, Convergent Ventures, and DegiTx Partners.
Matthew Guiney, CFO, Flybridge Capital Partners. Flybridge Capital Partners, a venture capital firm focused on AI and SaaS-driven businesses, continues to back ambitious, high-growth companies. Under Matt Guiney’s financial leadership, the firm has made strategic investments in the next generation of AI-first businesses, highlighted by Flybridge’s investment in Nasuni, a cloud storage company. Flybridge sees venture capital as a “people business” and the importance of the founder qualities in early-stage investments.
Raj Jalan, CEO, Device42. Freshworks Inc. completed its June 2024 acquisition of Device42, marking a major milestone in IT Asset Management. Raj’s leadership positioned Device42 as a leader in infrastructure discovery and dependency mapping, which will now enhance Freshworks’ IT Service Management platform. This integration will provide customers with advanced asset tracking, risk management, and faster incident resolution.
Meghan Joyce, Co-Founder & CEO, Duckbill. Duckbill, the Boston-based AI-powered personal assistant platform, secured $33 million in seed and Series A funding, led by Forerunner Ventures, with participation from Greycroft, General Catalyst, Bain & Company’s Future Back Ventures, and others. The funding will drive Duckbill’s expansion and continued development, integrating human intuition with AI-driven efficiency to revolutionize how people manage tasks and schedules.
Kevin McCarthy and Chris LeRoy, Managing Directors at Truck 9 Partners, and Marty Mazzella, CEO of Ti-SALES, LLC. For Marty, it’s never too late to jump in — and he’s quick to credit the great people he’s surrounded himself with. For Chris and Kevin, humility runs deep — they got their start working in the trades while still in college. As they continue their pursuit of getting 1 percent better every day, they stay focused on people, challenge, and having fun along the way. Ti-SALES exemplifies that spirit. A leading distributor of waterworks and wastewater products since 1963, the company recently secured a significant investment from its management team and Truck 9 Partners — ensuring long-term growth while maintaining local ownership. The funding will enhance customer service, expand market reach, and support strategic initiatives to further strengthen Ti-SALES’ leadership across New England and New York.
Jakov Kucan, Chief Technology & Information Security Officer at Manifold. Manifold, an AI-driven research infrastructure company for biomedical science, raised $15 million in Series A funding, led by TQ Ventures, with support from Calibrate Ventures, SK Ventures, and TTCER Partners. Under Jakov’s leadership, Manifold’s Trusted Research Environment platform is enabling secure, large-scale data collaboration for top life sciences R&D organizations.
Jason Maxwell, CEO of MP: Wired for HR. MP: Wired for HR continues its national expansion with the acquisition of APS Workforce Management, significantly increasing its geographic footprint. Under Jason Maxwell’s leadership, MP has built a comprehensive human capital management platform that delivers industry-leading HR technology, compliance expertise, and white-glove service. The APS acquisition strengthens MP’s position as a premier HCM provider, ensuring businesses nationwide receive top-tier workforce solutions.
Jared Paquette, Chairman, Capstone Holdco LLC. Coming from a family of entrepreneurs, Jared actively seeks family-friendly businesses for long-term partnerships. Capstone Holdco is rapidly expanding its IT services platform, with the July 2024 acquisition of Retail Process Engineering, marking its second add-on under Conanicut Capital’s buy-and-build strategy. With a focus on merchandise management, they’ve built strong relationships with brands like L’Oréal and Tory Burch. Backed by deep supply chain IT and enterprise solutions expertise, Capstone and RPE are well-positioned to deliver best-in-class retail technology services to a growing enterprise customer base.
Michael Young, CEO of ConnectPay Payroll Services. Michael Young has built a reputation on trust and connection. Under his leadership, ConnectPay — a fast-growing payroll and tax compliance platform — has completed 37 acquisitions in just eight years, solidifying its position as a leader in small business payroll solutions. Michael continues to expand the company’s capabilities and partnerships, delivering integrated payroll, benefits, and tax support to businesses nationwide.
Social Impact Award Honoree
Renee Fry & Julie Fry, Co-Founders, Gentreo. Renee and Julie Fry bring their personal story and life experience to a mission that impacts people at one of life’s most critical moments. After seeing the need firsthand with a family member, they built Gentreo into a pioneering force in digital estate planning — making affordable, easy-to-use tools accessible to families across the country. Through their leadership, Gentreo bridges technology and financial services, simplifying what has traditionally been a complex and costly process. Estate planning is essential, yet many people avoid it due to cost or lack of access. Renee and Julie have combined their backgrounds in marketing, elder care, technology, and government affairs to lead a team that’s changing that reality.
Originally from State College, PA, and proud Penn State natives, Renee and Julie exemplify what it means to be long-term value creators. Their ability to scale Gentreo, secure strategic partnerships, raise capital and drive meaningful change in a traditionally slow-moving industry speaks to their vision, passion and perseverance. Their empathy and compassion fuel their drive to make estate planning accessible — helping families avoid disputes and financial loss. Thanks to their commitment to innovation and financial empowerment, Gentreo has transformed how families protect their legacies.
Dealmakers Hall of Fame Honorees
Anthony Basile, CEO of Catania Oils. Catania Oils has been a family business for over 100 years, growing from door-to-door olive oil sales in Boston’s North End into the Northeast’s leading processor and packager of plant-based oils found in many retailers and restaurants across the U.S. Under Anthony Basile’s leadership, the company has scaled to $500 million in revenue with 270 employees and expanded its manufacturing capabilities and product offerings. Most importantly, Anthony has been a family legacy linchpin as the third-generation leader who started working in the business as a young boy as the third generation to now seeing the fifth generation begin to work in the business.
Anthony has spearheaded investments in automation and sustainability, ensuring Catania remains competitive in an evolving market. He has also led major partnerships with national food distributors, restaurant chains and private-label retailers, further solidifying the company’s market position. Recognized as a forward-thinking executive, Anthony has balanced family tradition with modern business practices, maintaining the company’s commitment to quality, customer service, and long-term growth.
Beyond Catania, Anthony is an active supporter of local businesses and economic development in the region, working to promote job creation and industry innovation. His leadership has helped Catania evolve from a regional player into a national force in the edible oils industry.
Nick Grewal, CEO & President of ePropelled. Nick Grewal is a serial entrepreneur, investor and technology visionary, founding multiple high-tech companies, including Nashoba Networks, LifeCare Technologies, and ePropelled. His $100 million exit to Cisco Systems with Nashoba Networks is just one highlight of his impressive career.
Nick has also been deeply involved in venture capital, investing in over 40 high-tech companies through Onlake Investments and serving as a Venture Partner & Advisor at Data Point Capital. His expertise spans engineering, business development, and operations, making him a key figure in Boston’s tech and investment ecosystem.
Beyond business, Nick actively supports philanthropic causes through his family foundation, dedicating the past 25 years to charitable initiatives. Congratulations, Nick!
Tara Heath, Chief Legal Officer & General Counsel at The Boston Beer Company. Tara started her career at Boston Beer in 1996 — as a temp. Nearly 30 years later, she has risen to not only Chief Legal Officer, overseeing some of the company’s most significant transactions, but also leading a number of key areas across the business. She played a critical role in Boston Beer’s merger with Dogfish Head, the acquisition of breweries in Ohio and Pennsylvania, and the design of the Sam Adams Taprooms in Boston and Cincinnati as well as microbreweries Coney Island and Angel City on the West Coast. Her strategic insight and legal expertise have been integral to Boston Beer’s continued success and expansion in the craft beverage industry.
Under Tara’s leadership, the legal team has navigated complex regulatory environments, ensuring Boston Beer remains compliant and innovative in a highly competitive market. She has also been instrumental in expanding Boston Beer’s portfolio, including its move into hard seltzers, canned cocktails, and non-alcoholic beers, keeping the company at the forefront of consumer trends.
Tara is known for her commitment to fostering a strong company culture, mentoring future leaders, and advocating for diversity and inclusion in the legal and beverage industries. She takes an active role in building the “Brewing the American Dream” program to help aspiring entrepreneurs with Jim Koch. Her influence extends beyond the boardroom, as she actively supports industry-wide initiatives to modernize beverage laws and regulations. Her ability to balance legal risk with business growth has made her a key architect of Boston Beer’s long-term success. Also, Tara is a Certified Cicerone, recognized for selecting, paring and serving a wide range of beers.
Barznab Khan, President & CEO of Rawshon Group of Companies. Barznab founded the Rawshon Group of Companies as a college sophomore in 2004. His entrepreneurial journey started as an immigrant from Bangladesh. Over the past 20 years, he has grown it into a diverse portfolio spanning retail, real estate, pharmaceuticals and cannabis. His entrepreneur’s spirit is not limited to dealmaking but also to serving his employees and the community he is in.
One of his flagship brands, Richdale Food Shops, operates 85+ locations across Massachusetts. His success is directly attributed to him and his team knowing the community and meeting their needs. This has driven loyalty and continued success from the people he serves. Barznab also actively invests in commercial real estate and high-growth ventures, leveraging his background in finance and international business. To aid his employees, he acquired real estate and converted them into townhomes for them to live at an affordable price as no affordable housing was available to them. Recently, Barznab has expanded into cannabis and provides a safe, concierge experience to women and men. He also helps local bands such as the “The Elevators” showcase their message and exposure.
A lifelong learner, he pursued his MBA at Northeastern University and remains deeply involved in the business community, holding memberships with Vistage CEO Group, the Young Entrepreneur Council, and the Harvard Club of Boston.
David MacKeen, CEO of Eliassen Group. David has led Eliassen Group through an incredible period of growth, driving the company’s expansion through three private equity partnerships, most recently with Stone Point Capital, who he considers friends and connects like teammates. Since 2019, Eliassen has closed 12 M&A deals — and they aren’t slowing down.
David’s leadership and how he lives sets him apart. As a CEO, he strives to hire better than self, to ensure titles do not matter. “Everyone contributes” — at Eliasson, everyone is a spoke in the wheel with something to contribute to the growth. Dave sees himself as the one who oils and maintains that wheel to keep is running. This has earned him recognition among Staffing Industry Analysts' Top 100 for seven consecutive years and a place in the Staffing 100 Hall of Fame. He was also named Citizens Middle Market Executive of the Year by the Boston Business Journal and has been recognized with a WSJ/Deloitte Award.
Beyond business, David serves on the boards of Bentley Executive Club, Endicott College, St. John’s Prep, and the Van Noy Valor Foundation. When he’s not leading deals, he enjoys coaching and playing hockey, golfing and traveling with his family.
