We are industry leaders dedicated to transforming work lives

Doug

Doug Jackson

Co-Chief Executive Officer

Doug co-founded the company with a mission to empower individuals with the career tools and resources needed to transform their work lives.

As a former Vice President of Corporate Strategy at Monster Worldwide, Doug is a distinguished entrepreneur specializing in online marketing, career management, and product development. He holds a PhD in Educational Psychology from Stanford University and a dual major undergraduate degree in Computer Science and Psychology from the University of Western Ontario.

When Doug isn’t busy shaping BOLD into the world’s leading platform for work-life transformation, you might find him doing permaculture on his farm and agrotourism project in Puerto Rico, deep sea fishing, and spending quality time with his family.

Doug

Jamie Freundlich

Co-Chief Executive Officer

Jamie co-founded BOLD in 2004 with a vision to help people transform their work lives. He has 25 years of experience developing and managing innovative online businesses and products. He’s a former Vice President at Monster Worldwide and Founder and CEO of SIMPATIX, a recruitment management software company sold to Monster in 2000. Jamie holds an MBA in Marketing and Finance from the Kellogg School of Management and is a member of YPO (Young Presidents’ Organization).

On the personal side, Jamie enjoys surfing, tennis, softball, yoga, and spending time with his two sons.

Doug

Gary C. Hsueh

Chief Financial Officer

Gary is a seasoned executive with 20+ years of finance, operations, and transaction experience. Prior to joining BOLD, Gary was a co-founder and Managing Partner of Catapult Capital, a middle-market private equity firm based in San Francisco that invests in consumer internet and software businesses.

During his tenure at Catapult, Gary became the CFO of Grindr, the world’s largest LGBTQ-focused dating app. As Grindr’s CFO, he helped grow revenue and profits by over 80% and took Grindr public to list on the NYSE in 2022.

Prior to Catapult and Grindr, Gary was the Vice President and Global Head of Search Partnerships at Yahoo, where he led a team that sourced, managed, and executed Yahoo’s search distribution and search content partnerships globally.

Prior to Yahoo, Gary was a Vice President in the Technology Investment Banking Division at Goldman, Sachs & Co., where he advised on almost $90B in M&A and financing transactions, including the carve-out of Skype from eBay and the Tesla Motors IPO.

Gary holds an MBA from the UCLA Anderson School of Management and a BS in Industrial Engineering from Cal Poly San Luis Obispo, where he graduated with honors.

Doug

Sahil Sahni

Chief Product Officer

Sahil Sahni is an impact-driven product leader with a career dedicated to building software that creates economic opportunities for talent across the globe. As Chief Product Officer at BOLD, he leverages his extensive experience to make recruiting more successful for both talent and employers.

Before joining BOLD, Sahil was the product and business leader for Upwork’s flagship business, Talent Marketplace, responsible for 90%+ of the company’s revenue. Through product innovation, he contributed significantly to Upwork’s double-digit growth and led the scaling of Upwork’s ads and monetization business to multiple folds within 18 months.

Earlier in his career, Sahil co-founded and scaled AllyO, an AI/ML SaaS company that has reduced hiring time by 90% and enabled over 20M+ job interviews. Recognized as an award-winning HR tech product, AllyO grew to millions of users before being strategically merged with a talent management partner.

Sahil also played a key role in Meta’s Metaverse Leadership Team, developing future-of-work solutions and pioneering products in AR and VR. His professional journey includes working at top institutions like McKinsey, MIT, and Techstars, where he collaborated with industry leaders to advance technology for social and economic impact.

Sahil holds a PhD from MIT and a B.Tech. from IIT, both in engineering.

Doug

Steve Higbee

Chief Human Resources Officer

Steve has over 20 years of experience establishing core HR/People processes at scale and building organizational capabilities across multiple industries.

Prior to BOLD, Steve was with Match Group, the world’s leader in online dating, where he led the HR teams for brands such as Match.com, Hinge, OKCupid, and others during a period of rapid growth. In addition, Steve has held HR leadership roles at Intuit, PayPal, and Bank of America.

He is a leader who is laser-focused on building employee capabilities and helping organizations scale and change during times of growth and transformation. Steve holds an MBA and a BS in Finance from Brigham Young University.

When he’s not helping teammates excel in their careers, he enjoys serving in his church, working out at the gym, and playing pickleball or tennis.

Doug

Himanshu Gupta

Senior Vice President, Engineering & Head of Development

Himanshu, a seasoned technology executive with 30 years of experience in enterprise software development, heads BOLD’s development center in India. He has been instrumental in developing the core technology platform for BOLD’s suite of products and building a world-class technology team.

Prior to joining BOLD, Himanshu held executive leadership positions with Letsbuy, Nextag, ADP, and Infosys. He holds a Bachelor of Technology from the Indian Institute of Technology, Delhi.

When he is not busy solving a technology problem, Himanshu is usually found fooling around with his two kids, playing tennis, or watching a movie with his family.

Doug

Anita Natarajan

Senior Vice President, Operations & New Business

Anita is a growth-focused executive with experience in B2C e-commerce marketplaces in a variety of industries. She is a people-first P&L leader with a track record of growing new businesses, scaling for success in the $100M-$10B range. She leads operations and new business expansion at BOLD.

Prior to BOLD, Anita ran the Product Division and International Business Unit (40+ countries) at Blue Nile. Before joining Blue Nile in May 2020, Anita ran Uber’s global airports business, growing it as a profit engine for the rides business.

Prior to Uber, Anita was VP of Sales Operations at A Place for Mom, a senior living marketplace where in addition to operations, she focused her time on partnerships with healthcare providers to improve continuity of care for seniors. Before that, Anita was a Project Leader at Boston Consulting Group, working in travel, healthcare, retail consumer strategy, and non-profits. She started her career as an engineer at IBM, automating chip design for servers and game processors.

Anita holds an MBA from Tuck School of Business, Dartmouth, and a Bachelor’s degree in Computer Engineering from Georgia Institute of Technology.

Doug

Nelson Ortiz

Senior Vice President, Global Accounting & Operations

Nelson is a seasoned accounting veteran with over 20 years of experience in global companies. He leads the global accounting, tax, treasury, and controllership for BOLD. He also focuses on operational efficiencies, corporate governance, the online payments sector as well as M&A activity.

Prior to BOLD, Nelson worked for multinational corporations such as Liberty Mutual and AIG in New York, Bermuda, and Latin America where he focused on controllership functions, building solid processes and financial reporting in multiple jurisdictions. Nelson attended Rutgers University and holds a Bachelor of Science in Accounting from the Interamerican University of Puerto Rico.

When not ensuring controls are in place, you can find Nelson boating in the Caribbean with his wife and three daughters.

Board Members

Doug

Ishmael Chawla

Technical Founder & Board Member

An internet technology professional with nearly 20 years of experience, Ishmael serves in a strategic technology advisory role. Prior to this, Ishmael established our India development center and set up our technical architecture. Before BOLD, Ishmael directed technology for one of the first web-based applicant management and resume tracking systems for Simpatix, which later became part of Monster.com. He also worked as a financial services technology consultant in New York for Accenture. Ishmael is a graduate of Amherst College, where he studied Computer Science and Russian Literature.