OpenView Venture Partners

About

OpenView Venture Partners is a Boston-based expansion-stage venture capital firm founded in 2006 by Scott Maxwell ¹. The firm’s singular focus is business software companies that have achieved early product-market fit and are ready to scale — what OpenView calls the “expansion stage” ².

Maxwell founded OpenView after six years at Insight Venture Partners, where he joined in 2000 as Chief Operating Officer and later led deal work, investing in eight portfolio companies ³. Prior to Insight, Maxwell held senior roles at Putnam Investments (Managing Director of Corporate Development) and Lehman Brothers (Senior Vice President and CFO of the Global Equity Division), and worked as a management consultant at McKinsey & Company ³. He holds a PhD in Mechanical Engineering and an MBA from MIT’s Sloan School of Management, plus MS and BS degrees in Mechanical Engineering from UC Davis ³.

OpenView is headquartered at 125 High Street, 2nd Floor, Boston, MA 02110 ⁴. The firm has raised $2.4 billion in total across seven funds since its founding ⁵. Key fund milestones:

• Fund III (2012): $200 million, oversubscribed, exceeded $150 million target ⁶
• Fund IV (2014): $250 million, oversubscribed, bringing total AUM to approximately $700 million ⁷
• Fund VI (2020): $450 million, oversubscribed at hard cap, approximately 50% larger than Fund V ⁸
• Fund VII (2023): $570 million, largest fund to date, 25% increase over Fund VI ⁵

In December 2023, OpenView announced it would suspend making new investments in Fund VII and instead focus resources on its existing portfolio companies, citing this as “the right thing to do strategically and as a fiduciary of our LPs’ capital” ⁹. The announcement was accompanied by a broad-based internal restructuring that significantly reduced staffing levels ⁹. Reporting in March 2024 indicated OpenView planned to return approximately 75% of the $571 million fund to its limited partners by Q3 2024 and use the remaining capital to support approximately 30 existing portfolio companies ¹⁰.

The firm’s limited partners include endowments, pensions, foundations, and financial institutions ⁸. At its peak, OpenView operated with approximately 80 team members maintaining a roughly 2.5-to-1 ratio of staff to portfolio companies ⁵.

Stated Thesis

OpenView publicly describes its investment focus as “high-conviction, concentrated venture investments in business software companies on the path to be large and enduring businesses” ⁸. The firm invests globally across infrastructure, applications, cybersecurity, and vertical software ⁵.

The firm’s defining intellectual contribution to venture and B2B software is the concept of “product-led growth” (PLG) — a term coined by OpenView Partner Blake Bartlett in May 2016 ¹¹. Bartlett defined PLG as “a go-to-market strategy that relies on product features and usage as the primary drivers of customer acquisition, retention and expansion” ¹¹. The thesis holds that when friction is removed from the user’s path to value, companies achieve superior growth economics compared to sales-led models ¹¹.

OpenView has been particularly enthusiastic about PLG companies. In announcing Fund VI, Partner Mackey Craven stated: “We are particularly enthusiastic about businesses like Datadog and Calendly that embrace product led growth” ⁸.

The firm targets seven to nine new investments per year per its own description, describing this as a “concentrated approach that allows us to meaningfully support our portfolio companies post-investment” ¹².

Scott Maxwell articulated the firm’s foundational investment philosophy: “If you don’t know where you are going, any road will get you there. By extension, if you do know where you are going, you can pick the best roads to get you there. That’s OpenView.” ³

The expansion stage — companies generating approximately $2–$20 million in annual recurring revenue with early product-market fit and repeatable go-to-market — is where OpenView concentrates ⁶.

Inferred Thesis

Based on 30+ verified portfolio investments across the firm’s history, the following patterns emerge. (Note: OpenView’s publicly listed current portfolio is approximately 78 companies as of late 2025 ¹²; this table represents a substantial subset. Percentages below should be read as directional given partial data.)

Sector distribution (from 30 verified investments in the portfolio table below): - Enterprise software / SaaS (horizontal): 14 of 30 (47%) — Datadog, Expensify, Highspot, Calendly, UserTesting, Postscript, Buildkite, Cypress.io, GitPrime, Workfront, Spredfast, Signpost, Socrata, Logz.io - Vertical SaaS: 8 of 30 (27%) — Deputy, VTS, Kareo/Tebra, Mangomint, FieldAware, Encamp, Paperless Parts, Optimize.Health - Infrastructure / developer tools: 4 of 30 (13%) — JumpCloud, Intezer, Balena, Scalr - Security / identity: 2 of 30 (7%) — Axonius, Kolide - Fintech / payments: 2 of 30 (7%) — Chargeflow, Pipefy

Stage distribution: OpenView consistently invests at Series B and Series C, which are true to its “expansion stage” branding. Tracxn data indicates 25 Series B investments with average round size of $19.1M and 14 Series C investments with average round size of $28.4M ¹². OpenView led the Deputy Series A ($25M) in 2017 as an exception — that portfolio company later became a unicorn in 2024 ¹³.

Check size: Typical lead checks of $15–$31M at Series B/C, consistent across Datadog Series B ($15M led), VTS Series B ($21M led), Expensify Series C ($17.5M led), and Deputy Series A ($25M led) ^14151613.

PLG pattern: The most notable pattern in OpenView’s portfolio that diverges from its stated thesis is how heavily the portfolio skews toward product-led companies. Datadog, Calendly, Expensify, Highspot, Postscript, Buildkite, Cypress.io, Voiceflow — all are PLG-native or PLG-adjacent. This is not merely stated — OpenView coined the term PLG and built an entire content and community apparatus (annual SaaS Benchmarks report, annual Product Benchmarks report) to identify and attract PLG companies ¹⁷¹⁸.

Geographic concentration: Despite positioning as a global investor, the portfolio skews heavily toward North America. The few international investments (Deputy in Australia, Pipefy in Brazil, Voiceflow in Canada) represent a meaningful minority. The firm operates out of Boston with secondary presence in New York ⁴.

Founder profile patterns: OpenView has repeatedly backed technically sophisticated products solving B2B workflow problems — expense management, workforce scheduling, commercial real estate, API management, cloud monitoring. Technical complexity in the core product appears to be a consistent through-line more than founder pedigree.

Co-investor patterns: OpenView frequently co-invests with Index Ventures (Datadog Series B), Accel (UserTesting Series C), ICONIQ (Calendly Series B, Highspot Series D), IVP (Deputy Series B), and Bessemer Venture Partners (Instructure Series D) ^198201321.

What they say vs. what they do: OpenView’s stated thesis emphasizes a global focus; the portfolio is predominantly North American. The stated thesis does not emphasize sector specificity, but the actual portfolio is highly concentrated in horizontal B2B SaaS and vertical software. The PLG lens is the clearest through-line between stated and actual investment behavior.

Portfolio

This table represents approximately 30 of 78 publicly known portfolio companies (~38%). OpenView reports 9 unicorns, 2 major IPOs (Datadog, Expensify), 35+ acquisitions, and 78 total investments as of late 2025 ¹².

In Their Own Words

Scott Maxwell, Founder and Managing Partner, on the firm’s differentiated focus:

“What makes OpenView unique is our focus. No other venture firm has our dedicated stage and sector focus.” ⁷

Scott Maxwell on the firm’s investment philosophy:

“If you don’t know where you are going, any road will get you there. By extension, if you do know where you are going, you can pick the best roads to get you there. That’s OpenView.” ³

Mackey Craven, Partner, announcing Fund VII (March 2023):

“As we have for nearly two decades, we remain focused on identifying and supporting innovative business software companies in high-growth product markets primed for rapid expansion.” ⁵

Mackey Craven, on the product-led growth portfolio thesis, Fund VI announcement (2020):

“We are particularly enthusiastic about businesses like Datadog and Calendly that embrace product led growth.” ⁸

Blake Bartlett, Partner, on OpenView’s PLG-focused content strategy:

“OpenView’s content exists to help companies in an operationally focused way, not just to fill the top of the funnel for their investment team.” ¹¹

Blake Bartlett, coining the product-led growth definition in 2016:

“[PLG is] a go-to-market strategy that relies on product features and usage as the primary drivers of customer acquisition, retention and expansion.” ¹¹

Blake Bartlett, on Voiceflow’s investment (August 2023):

“Voiceflow has not only introduced an innovative solution, it has seeded massive demand from name brand businesses looking to design, prototype, and build conversational AI agents.” ³⁰

Mackey Craven, on the UserTesting investment (2015):

“UserTesting gives anyone designing a digital experience access to feedback from real users on demand.” ¹⁹

Scott Maxwell, on the Mashery investment:

“As API Management emerges as a business-critical technology, we remain committed to the Mashery team’s unique strategy of partnering with brands to help them leverage APIs for business growth.” ²⁵

What Founders Say

Tope Awotona, CEO and Founder, Calendly, on OpenView’s value as an investor:

“OpenView brings a unique perspective to their work with Calendly and has been a huge factor in our success. Many of the introductions provided through their extensive network have turned into advisors or employees at Calendly.” ⁴

Oren Michels, CEO and Co-Founder, Mashery, on OpenView’s operational support:

“OpenView gave us the objective market and customer analysis we needed. They delivered recommendations and meaningful data that have influenced almost every component of our organization.” ⁷

Oren Michels, CEO and Co-Founder, Mashery, on OpenView’s sales-focused support:

“OpenView’s sales expertise has allowed us to expand our sales funnel across the country.” ⁶

Braden Ream, Founder and CEO, Voiceflow, on working with OpenView:

“We are excited to work with the OpenView team, which brings unmatched experience working with businesses like ours.” ³⁰

Darrell Benatar, CEO, UserTesting, on the firm’s vision for the company at the time of their investment:

“This financing is going to help user experience testing become ubiquitous, so that all design will be user-centered design.” ¹⁹

Sources