I am thrilled to announce that our Work-Bench portfolio company RippleMatch has raised a $23.5M funding round led by Invus Opportunities.

Behind this exciting headline, I want to share some of the untold grit and creativity behind RippleMatch’s journey that led to this milestone.

When we invested in RippleMatch back in 2019, it was behind the thesis that the traditional career fair system was not only broken, but biased. While career fairs were still the status quo for many companies, in speaking with our greater Work-Bench network, many forward thinking companies had already realized they could not meet all of…


The Work-Bench Snapshot Series explores a particular topic we’re digging into from an investment standpoint.

We did a deep dive into the procurement space back in 2019, when there had already been years of discussions over the need for tooling to support digitization in the function.

Yet a recent McKinsey report indicates that the market adoption of procurement software has been slow: “many [companies were] trapped in pilot purgatory, making small investments in select use cases that never scale[d] up to achieve real business impact.”

Fast forward to today, COVID-19 has exposed new pressures and strains on the procurement industry…


Happy International Women’s Day! There is a lot to celebrate today as more efforts, organizations, platforms, and networks exist than ever before in supporting female entrepreneurs and founders, and dedicated to enacting change and inclusivity for the VC and tech ecosystem.

However, when we announced our portfolio company Spring Health’s Series B in November 2020 we were reminded of a depressing industry statistic: according to Pitchbook, only 5% of female entrepreneurs go on to raise Series B financings. And according to Fortune, 2020 actually widened the inequality gap, with female founded companies receiving only 2.2% of the year’s total venture…


As early-stage enterprise software investors with an obsession with go-to-market strategy, Work-Bench has worked with dozens of enterprise founders and sales leaders navigating the tricky process of pricing.

At the early stage, so many founders are tempted to underprice their product in order to win early deals (and compete with legacy vendor’s higher pricing). However, it’s important to thoughtfully create a pricing framework that can scale with your product and go-to-market motions over time.

This Enterprise Playbook focuses on a tactic we uncovered with many of our later-stage, fast-growth companies: a value-based pricing calculator, that can help answer:

  • How do…


A new year means 9 full years of hosting the NY Enterprise Tech Meetup (NYETM) and a new epic lineup of 2021 speakers. This month, we kicked off 2021 with a NYETM in partnership with Sequoia Capital, featuring an anticipated fireside chat with Todd Mckinnon, Co-Founder and CEO of Okta.

It’s certainly been a wild 12 year ride for the Okta team, having raised over $225M in funding, an IPO in 2017, and over $580M in revenue today. Todd shared with us his top lessons from closing their 1st, 10th, and 50th customer, and what it took to get here…


Like much of the country, New York City has experienced its share of battle scars in 2020 from the pandemic, causing a lot of questions around whether or not NYC’s startup ecosystem will survive.

As longtime NYC enterprise software investors here at Work-Bench, we turned to the numbers to understand the impact that the pandemic has had on NYC’s enterprise community. While we’re not out of the woods yet, our 2H 2020 NYC Enterprise Tech Funding Report showed NYC enterprise tech had its best year yet, with $5.8B raised in 2020 in 189 deals, far outpacing the $3.3B …


We often describe our Enterprise Roundtables, Playbook Lunches and other Work-Bench community events a little bit like therapy — a place to connect, share best practices, air out top challenges, and find others who have solved similar pain points.

Our recent Women in Enterprise Sales Forum was no different. …


As enterprise investors here at Work-Bench, investing at Seed II stage, we are obsessed with all things go-to-market and working alongside our founders to refine their early GTM and sales engine.

Over the years, we’ve noticed different startups have different ways of presenting this information at a high-level for their recurring investors catchups, internal meetings or to prospective investors. While there’s no one right format, there are specific pieces of information that can help set up a more productive conversation around your sales and where they are heading.

There are many blog posts out there that cover SaaS metrics in-depth…


I had such a blast chatting with Harry Stebbings on the SaaStr Podcast last week (yes, he is just as fun and amazing as he sounds :)

Listen to the full SaaStr #331 Episode here.

While my co-founder Jonathan Lehr was featured on the SaaStr Podcast back in 2017 talking about ins and outs of Work-Bench’s corporate model, this time around Harry and I focused specifically on enterprise sales strategy and tactics during the time of COVID-19:

  • How should founders expect to see their new business pipeline be impacted by COVID-19?
  • What’s the best way to structure enterprise pipeline reviews?
  • How should startup sales leaders engage with new…


There continues to be a lot of uncertainty in the market as we simultaneously face a global health pandemic and an economic crisis. To combat this uncertainty, we have been hosting a series of “Weathering the Storm: 2008 & Now” webinars that provide tactical guidance for our enterprise community of startups, corporate executives, and investors.

To showcase different perspectives, we’ve featured Fortune 500 IT buyers, enterprise founders, and most recently in our third session, we spoke with Kelly Breslin Wright, former Executive Vice President of Sales at Tableau. She helped build and scale Tableau for 12 years from $0 to…

Jessica Lin

co-founder & VC @Work_Bench | GED educator | rethinking work

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