Len Jordan

Len joined Madrona in January 2010. He is interested in software, hardware, and analytics systems that transform work and economics for big industries and consumer products that change how we see, hear, feel, and sense life. He most enjoys working with entrepreneurs on building their teams to last and scale.

Journey to Madrona

Len has served on the boards of 20+ early-stage companies and has been a director or executive at three companies that have completed initial public offerings. Before joining Madrona, Len was a partner at Frazier Technology Ventures, where he was directly involved in several investments, including Control4 and DocuSign. Prior to his career in venture, Len spent 16 years in the software industry, including as senior vice president at RealNetworks from 1996-2001 (RNWK-Nasdaq). Len’s team released four major versions of the RealSystem software platform and generated the majority of the company’s more than 100% annual revenue growth during the period. Before joining RealNetworks, Len was president of Creative Multimedia, Inc. (acquired by IHS- NYSE INFO). He started his software career in product management for Central Point Software before it was acquired by Symantec (SYMC- Nasdaq).

Lessons learned

  1. Breakthrough technology and market ideas should make you a little uncomfortable. Disruptive products that revolutionize the way people do things will include risk. Identifying the risks and developing execution plans to overcome them is crucial.
  2. Investing in a compelling initial market, product, and strategy is important. But markets, customer dynamics, platforms, and competition will change, so the essential factor is backing a team with exceptional abilities to consistently identify new market opportunities, products, and go-to-market strategies to reach them. The people who create, reinvent and execute the playbook are more important than the playbook.

When he’s not in the office…

Len is past president of the Seattle Country Day School Board of Trustees, a founding board member of Seattle United Soccer Club, and has coached and played soccer his entire life. He enjoys spending time trying to keep up with his four children, runs occasionally and is remembering how to play tennis.

Noteworthy

Len graduated magna cum laude from the Eccles School of Business at the University of Utah with bachelor’s degrees in finance and economics.

Alexandra Estep

Alex joined Madrona in 2023 and serves as the firm’s controller. In this role, she supports the finance, accounting, tax, and audit functions for Madrona and Madrona’s funds.

Journey to Madrona

Before joining Madrona, Alex was an engagement manager at Standish Management, a fund administration firm specializing in outsourced CFO and back-office support serving clients across the private equity industry. She began her career with Standish as an associate and helped grow the company, specifically their Seattle office, over nearly seven years.

When she’s not in the office

Outside of work, Alex enjoys walking her dogs in West Seattle, trying new restaurants, curling up with a good book, and playing tennis. She also loves to travel, whether it’s discovering new places or revisiting familiar favorites.

Noteworthy

Alex studied at the University of Washington in Seattle, earning economics and political science degrees.

Rachel Flink

Rachel joined Madrona in the fall of 2015 as an executive assistant and later transitioned into her current role as operations administrator. In her support of the back office, Rachel manages Madrona’s weekly partnership meeting calendar, helps maintain Madrona’s investor database, assists in processing capital calls and distributions, organizes various events, and provides day-to-day administrative support to Jennifer Chambers and Troy Cichos.

Journey to Madrona

Before joining Madrona, Rachel worked alongside and supported the founder of a Seattle area startup. Working alongside the company’s leadership team for five years, Rachel got a close look at the peaks and valleys that come with building a first-of-its-kind company. Because of this experience, Rachel greatly admires the founders that come to Madrona with such enthusiasm to build something new.

When she’s not in the office…

Rachel loves to spend time out and about with her husband and friends. And as much as she enjoys being on the go, she equally craves a quiet weekend at home working in the yard, ordering takeout, and bingeing the latest series curled up on the couch.

Noteworthy

Rachel attended Highline College, where she obtained an associate degree in administrative management.

Stella Fosberg

Stella joined Madrona in August 2023 as a receptionist and transitioned to the role of portfolio administrator in 2025. In her current position, she supports the back-office team with a focus on the investment side, ensuring Madrona maintains accurate and up-to-date data across all portfolio companies.

Journey to Madrona

Stella graduated from Boise State University in 2023 with a bachelor’s in finance. Stella was drawn to Madrona because of her love of finance and numbers.

When she’s not in the office

Stella enjoys playing and watching various sports and wants to learn how to make tasty and healthy dinner recipes. Stella was born and raised in the Seattle area, and she loves exploring everything the city offers.

Noteworthy

While Stella was a student at Boise State University, she worked as a lifeguard at the campus recreation center and was a member of the club tennis team and the Zeta Tau Alpha sorority.

Coral Garnick Ducken

Coral joined the team in 2022 to help tell the stories of Madrona and its portfolio companies.

Journey to Madrona

Coral covered business news in the Seattle area for seven years. At the Seattle Times, Coral covered the Port of Seattle, T-Mobile, and various other business news topics. As a Business Reporter who covered breaking news on the weekends, Coral was part of the team to receive a Pulitzer Prize for the Seattle Times’s coverage of the tragic Oso landslide that struck Saturday, March 22, 2014. At the Puget Sound Business Journal, Coral covered health care and retail, which included writing about companies like Starbucks, Nordstrom, Costco, Juno, and Seattle Genetics, as well as the work coming out of the Fred Hutch and the University of Washington. Coral partnered with another reporter on a year-long project to document the cost of homelessness in Seattle, receiving a Sigma Delta Chi award from the Society of Professional Journalism for that coverage.

Lessons learned

Telling your story can be very difficult but going through the process of putting it into words provides so much clarity. Every founder — everyone in a company, really — should be able to tell the founding story and the problem a company is solving in a way everyone — even the non-technical —can understand.

When she’s not in the office…

As an Alaskan who grew up in a small fishing village in Southeast Alaska, being on the water is in Coral’s blood. You can often find her taking advantage of the area’s quick access to the Puget Sound, the coast, Lake Union and Lake Washington to jump in her kayak, head out on the boat to go crabbing, or driving to Westport to go clamming during an opening. Coral also loves camping, hiking, and bouldering.

Noteworthy

Coral graduated from Western Washington University with a bachelor’s in journalism in 2009. In 2013, she graduated from Columbia University with a master’s in journalism. Coral is most proud of her time as a Peace Corps volunteer in Honduras.

Gerald Grinstein

Jerry returned to Madrona as a strategic director in late 2007 after a leave of absence serving as CEO of Delta Air Lines for almost four years. A co-founder of Madrona Investment Group, Jerry served on the board of portfolio company Expedia.com. “Some of our most successful entrepreneurs are really inventors at heart. I think of Madrona not only as a source of capital but of business strength that takes an innovation and moves it into the marketplace.”

He is the former non-executive chairman of Agilent Technologies and former chairman and CEO of Burlington Northern Inc. (BNI), where he oversaw the company’s acquisition of Santa Fe Pacific Corporation, which created the nation’s largest railroad. Prior to joining BNI, he held positions including chairman and CEO of Western Airlines, partner in the law firm Preston, Torgrimson, Ellis & Hollman, chief counsel to the United States Senate Commerce Committee, counsel to the Merchant Marine & Transportation Subcommittee, and administrative assistant to U.S. Senator Warren G. Magnuson.

Jerry is also a board member of the William D. Ruckelshaus Center.

A Seattle native, Jerry is a graduate of Yale University and Harvard Law School. When he is not at work, you may find him sneaking off to fly fish or trying a new restaurant.

Sunny Gupta

Sunny is the co-founder and CEO of Apptio.

Journey to Madrona

Sunny co-founded Apptio in 2007 with a customer obsession that led him to uncover significant untapped demand for pioneering a new software category (technology business management or TBM) — an analytics-based business management system for CIOs. Sunny led Apptio to an IPO in September 2016 and to its acquisition by Vista Equity Partners in January 2019 for $1.94B. Since going private with Vista, he has led four acquisitions, significantly expanded the customer base, expanded into international markets, and increased innovation.

Prior to founding Apptio, Sunny was EVP of products at Opsware. He was responsible for all product businesses until HP acquired Opsware in 2007. He was also the co-founder and CEO of iConclude, which pioneered the IT runbook automation market through its acquisition by Opsware. Previously, Sunny held senior leadership roles in products, business development, and engineering at Mercury Interactive, Rational Software, and IBM.

Lessons learned

  1. Unwavering commitment to a customer – listen, learn, and have the ability to change and morph based on customer feedback.
  2. Continuously focus on things that are breaking and not working well.
  3. Focus and reward on delivering results vs. efforts.

When he’s not in the office…

Sunny loves watching the Seattle Seahawks, riding his Peloton and keeping fit, and traveling and spending time with his two kids and wife.

Noteworthy

Sunny earned a bachelor’s in computer science from the University of South Carolina (Now Coastal Carolina University). He was named a “Top 40 CEO Under 40″ and was recognized as an Ernst & Young Entrepreneur of The Year 2012 Pacific Northwest. Sunny was named to the prestigious Puget Sound Business Journal Power 100 list for 2020 and 2021.

Sunny joined the Gainsight Board of Directors in May 2021, joined the board of Securonix in May of 2022, and serves as Strategic Advisory Board Member to the Foster School of Business at the University of Washington and Gupta College of Science at Coastal Carolina University.

Charlotte Hubbert

Charlotte is senior director, business development & strategic alliances at NanoString.

Journey to Madrona

Charlotte has over fifteen years of basic science research and over ten years of biotech venture investment experience across a broad range of sectors, therapeutic modalities, and stages. Charlotte has a proven ability to combine deep scientific expertise and business development acumen to identify innovative opportunities to drive returns and impact.

Prior to NanoString, Charlotte was partner and head of Gates Foundation Venture Capital, a $500M initiative at the Bill and Melinda Gates Foundation Strategic Investment Fund, where she oversaw investing in innovative technologies that supported the foundation’s programs in global health and agriculture. Notably, Charlotte led investments and served on the board of directors of Synlogic (Nasdaq: SYBX), Sera Prognostics, Lodo Therapeutics, Agtech Accelerator, Vedanta, and Vir Biotechnology (Nasdaq: VIR). Before joining the foundation, Charlotte was a vice president at H.I.G. BioVentures, investing broadly in healthcare. Charlotte began her career in early-stage biotech, investing at Accelerator Corporation, where she was part of the founding team and oversaw the management of several companies. Charlotte earned a bachelor’s in microbiology from the University of Washington and a Ph.D. in pharmacology and cancer biology from Duke University, for which she received the prestigious Harold Weintraub Award. She did her post-doctoral work in stem cells and regenerative medicine at the Institute for Stem Cells and Regenerative Medicine at UW.

Lesson learned

If you are the smartest person in the room, you’re not doing it right.

When she’s not in the office…

Charlotte enjoys spending time with her family and working on various music projects. She is an avid disaster film and book fan, so if you have a world-ending story, she wants to hear about it.

Noteworthy

Charlotte currently serves on the Board of Directors at City of Hope and Nuvara Health, and she was honored as a Fierce Woman in Biopharma 2016 by FiercePharma, and as a Leading Woman in Life Sciences 2016 by Life Science Washington. She is a member of the Kauffman Society of Fellows (Class 14) and has served on the board of Life Science Washington and the steering committees of the Fred Hutch Cancer Institute’s Evergreen Fund, UW Innovation Roundtable, and Columbia University Lab-to-Market initiative.

Nina Kapur

Nina joined Madrona in 2018 and focuses on the day-to-day accounting for the company while also handling investor relations in Madrona’s funds.

Journey to Madrona

Before joining the Madrona team, Nina worked for one of Puget Sound Business Journal’s Fastest Growing Private Companies – North Pacific Property Management, in the accounting department, primarily focusing on general accounting and other related duties.

When she’s not in the office…

Nina loves spending time with her family and friends and enjoys traveling any chance she can get. Born and raised in Browns Point, Nina is a huge fan of all that there is to offer here in the Pacific Northwest, and she can always be found near the water – especially in the Summer! While she often tends to stay pretty busy, nothing sounds better to her than going out for a nice dinner and then going home to relax and watch movies.

Noteworthy

Nina attended the University of Washington and graduated with a degree in political science and economics.

Lena Klassen

Lena has been with Madrona since 2016 and serves as Madrona’s IT Systems Analyst.

Journey to Madrona

Lena started her IT career at a midsize enterprise in Canada, where she discovered her interest in helping others become productive and successful technology users. She has worked in the information technology space since 2012 and has since developed a passion for user experience-focused systems and security.

Lessons learned

IT systems, software, and processes need to be designed with the user, not just for the user, if we want people to adopt them.

When she’s not in the office…

Lena is a podcast enthusiast and recent Matcha latte convert who enjoys exploring the Seattle food scene. Current podcast favorites include Ologies, 99% Invisible, and Founded and Funded.

Noteworthy

Lena graduated with honors from the University of Toronto, where she developed her passion for systems thinking and user experience design.

Ted Kummert

Ted is now in his third chapter at Madrona, having transitioned from his role as chief product development officer at UiPath in early 2023. Ted brings decades of experience leading high-performing product and engineering teams to the venture partner role, where he focuses on evaluating new investments and advising portfolio companies and their leaders. Ted is passionate about the enterprise and focuses on investments in infrastructure & platforms, data & analytics, and intelligent applications.

Journey to Madrona

Ted first joined Madrona in 2013 as he ended a 23+ year career at Microsoft. He held several roles leading development organizations that built operating systems, consumer online services, enterprise security, enterprise application platforms, and data platforms. In his last role, he was corporate vice president of Microsoft’s Data Platform Group. He led the development of several key Microsoft enterprise products, including SQL Server, SQL Server Parallel Data Warehouse, SQL Azure, and Microsoft’s business intelligence and big data offerings. Prior to Microsoft, Ted worked as an engineer for Apple and Hewlett-Packard.

After his first chapter at Madrona, Ted joined Apptio — a Madrona portfolio company that created the Technology Business Management category. During his four years at Apptio, which included Apptio’s successful IPO in 2016, Ted built a world-class engineering and product team and transformed Apptio’s core platform from a custom solution to distinct SaaS applications, extending Apptio’s market and product portfolio.

After his second chapter at Madrona, Ted joined UiPath in early 2020 as chief product development officer. UiPath is a pioneer and leader in the RPA category and was also a Madrona portfolio company. At UiPath, Ted was responsible for the vision and strategy for UiPath’s automation platform and delivering that for both customer-managed software deployments and via the Automation Cloud, UiPath’s multi-tenant SaaS offering. In addition to his core responsibility of leading products and engineering, Ted was also responsible for IT, security & trust, and product support. During his three-year tenure, which included UiPath’s successful IPO in 2021, he led a major platform expansion that included multiple acquisitions.

Lessons learned

  1. Software is a people business. If you study the most successful software companies, you will always find they have incredible people and an environment that lets them do their best work.
  2. Pay attention to your muscles. Many failures to “maximize your opportunity” come when you failed to evolve your processes and capabilities to your new reality – whether that’s the number of products, the size of your team, the size of your code base, the size of your business, or related to a new delivery model.
  3. Have fun. Software companies are uniquely intense – what other industries so frequently self-disrupt? We do it because we love the intensity, but you also need to pay attention to the long game. Maintain balance in your life, and remember to take a breath and have fun.

When he’s not in the office…

Ted is a rabid soccer and Sounders fan. He loves to run and exercise, which also helps with his love of great food and wine. He and his wife, Pam, raised three boys that are all on their own, but they spend as much time with them as possible.

Noteworthy

Ted is a passionate Husky and graduate of the UW electrical engineering department, where he currently chairs their Industry Advisory Board.

Andrew Leary

Andrew joined Madrona in 2025 and serves as our IT support engineer.

Journey to Madrona

Andrew gained his interest in troubleshooting and assisting others with technology while working at the Apple Store’s Genius Bar. He has been working in Information Technology since 2018 and is looking forward to continuing to grow and expand his knowledge in the field.

Lessons learned

Tailoring support to users with varying levels of technical experience is crucial. By meeting people where they are — whether they’re tech-savvy or brand new — empathy and clear communication are just as important as technical know-how.

When he’s not in the office…

Andrew enjoys following his favorite Bay Area sports teams — the Warriors, 49ers, and Giants — and rarely misses a game. You may also catch him and his wife walking their two cats on leashes in one of the many nearby parks.

Noteworthy

Andrew grew up in the Sacramento area and has been with his wife since they started dating in high school. After graduating from Sonoma State University with a bachelor’s degree in history, Andrew and his wife embarked on a new adventure and moved to Seattle in 2019.

 

Daniel Li

Dan joined Madrona in 2015 and became a venture partner in 2021 when he co-founded Plus, a Madrona portfolio company that allows users to automate their reporting workflows using AI.

Journey to Madrona

Prior to joining Madrona, Dan worked at the Boston Consulting Group. At BCG, Daniel worked on strategy and technology projects, from developing go-to-market strategies for cloud vendors to deploying new technology systems to improve insurance claims processing.

Lessons learned

  1. Being a founder is hard. No one really sees the day-to-day data or feels the ups and downs the same way you do, but great investors can be a sounding board to help you zoom out and focus on the things that matter the most.
  2. Find the right environment to do great work. You’ll do your best work and be happiest when you work with people you enjoy working with, solve problems you are passionate about, and make sure you are always learning new things.
  3. Don’t waste your time on decisions everyone else has already made. There are plenty of exceptions to the rules, especially in the startup world. But you’ll save a lot of time trying conventional wisdom first (e.g., ship early, spend more time talking to customers, picking SaaS tools) and then identifying the key areas where you want to be different.

While he’s not in the office…

Dan loves reading science fiction, trying new restaurants, and trying to stay fit on his bike. He is also active in the Seattle community and founded the Pacific Science Center’s Associate Board.

Noteworthy

Dan graduated summa cum laude from the University of Pennsylvania with majors in finance, psychology, and international studies.

Alison McCulloch

Alison joined the Madrona team in November of 1999. She supports Matt McIlwain, Jeff Mills, and Paul Goodrich. As a longstanding member of the team, Alison also drives important corporate event planning and assists the communications and marketing team with social media, photo editing, and more.

Journey to Madrona

Prior to joining Madrona, Alison worked in the insurance industry at a small family-owned agency, followed by the transportation and logistics industry as an ocean import technician at FedEx, formerly Tower Group International, owning accounts for clients like Kawasaki Motors and Uwajimaya.

When she’s not in the office…

Alison enjoys hiking, gardening, home improvement projects, taking her pup to the dog park, coffee sipping, book reading, music listening and Peloton riding.

Noteworthy

Before moving to the Pacific Northwest, Alison attended university on the East Coast at SUNY Brockport, where she obtained a bachelor’s in psychology.

Jeff Mills

Jeff Mills joined Madrona in 2024 as investor relations partner. Jeff works with Madrona’s global investor base of foundations, family offices, and endowments.

Journey to Madrona

Jeff brings more than 25 years of experience in fundraising, marketing, client service, and management to the firm. He has held a variety of roles in the alternative investment market, including Gryphon Investors, Resource Capital Funds, Brooklands Capital Strategies (a division of TPG Capital). Ares Management, Oak Hill, and Probitas Partners.

Lessons learned

Slow down and keep it simple. Focus on delivering exceptional results and service to your investors. People and culture matter (and yes, culture eats strategy for breakfast!). Have fun along the way.

When he’s not in the office

Jeff enjoys spending time with his wife and two sons (and dog!) in any outdoor activity. In addition to his desire to ski more, he is an aspiring swimmer and cyclist as he transitions to lower-impact sports. He is an avid non-fiction reader and podcast listener, who is also a creative “leftover” connoisseur finding the deep recesses of the refrigerator and freezer on this quest. He is an enthusiastic supporter of all things Army West Point – GO ARMY, beat Navy!!

Noteworthy

Before his fundraising career, Jeff was an aviation officer in the U.S. Army, where he served as a helicopter pilot, including a stint as a company commander, for seven years throughout the U.S. and South Korea.

He received his bachelor’s from the United States Military Academy at West Point, and his MBA, finance and strategy, from The University of Chicago Booth School of Business.