Welcoming Randi Jakubowitz to the 645 Ventures’ Success Team

Welcoming Randi Jakubowitz to the 645 Ventures’ Success Team

May 4, 2022

Welcoming Randi Jakubowitz to the 645 Ventures’ Success Team

We’re excited to announce that Randi Jakubowitz has joined 645 Ventures as Head of Talent and the newest member of our Success Team.

We’ve seen first-hand the competitiveness of the current job market. As an early-stage investor, we constantly emphasize to our portfolio founders the critical need to hire purposefully, strategically, and build cultures where talented people love to work. The best candidates seldomly hit the open market, executive recruiters are inundated with requests, and retaining the best talent has become a core priority amongst the most successful and competitive tech companies. In February of this year, there were 20k tech-related job postings from New York employers, up about 30% YoY, according to data tracked by CompTIA. But for NY based tech companies, the challenges do not stop there. With remote work seemingly here to stay, local startups and tech companies are being forced to compete in a national job market—which had a record 400k openings last month.

This external data has been echoed and confirmed within our own portfolio. In a recent announcement for our newest 645 engineer Justin Fargione, we provided a peek behind the curtain of 645’s proprietary software Voyager. In that post, we discussed how Voyager has given 645 an advantage on how we discover, track, and evaluate startups in the ecosystem; however we did not go into detail about how Voyager has helped us drive value for the companies in our portfolio. Post-investment, we leverage Voyager to allow us to move quickly on portfolio requests and use shared historical learnings to detect potential areas of need before they occur. Voyager also allows us to track where we are providing value to our companies and where we could be falling short.  We track requests at this level to understand what is needed by early stage founders across our ecosystem and where potential gaps in our offerings exist.

Value Add Tasks by Category


October 2021 (Trailing 90 Days)

Above is a look at our data output in October 2021 for the trailing three months. Recruiting/HR was the most commonly cited category for new value add tasks from founders in our network. Also, it was the category with the highest failure rate on our end. As our team began to lead more seed and Series A rounds and other portfolio companies started to blitzscale to the growth stage, significant headcount growth and demand for more specialized talent was reflected in the data from our Voyager software. As the data demonstrated an accelerating need, it was clear that bringing on a head of talent would help us become better partners to our founders.

This data snapshot kicked off an effort to prioritize the hiring of a Head of Talent to partner with our founders to tackle these unique and critical challenges. When our portfolio is hiring for themselves, we stress the importance of building scalable processes to repeatedly make A+ hires, particularly in the early days. Those hires shape culture, challenge thinking, and attract the same caliber of talent in a compounding effect that can pay dividends for years to come.

At 645, we do our best to practice what we preach. As we ramped up the search to hire a Head of Talent in late 2021, it seemed only right to apply the same mentality of purpose, strategy, and rigor to our process that we recommend to our portfolio founders. We were seeking a free thinker, a proven leader, and someone who was willing to challenge the status quo to build a first-class VC talent offering. Our process comprised a combination of network-driven and outbound efforts, enabling us to evaluate dozens of candidates. We chose not to hire a recruiter for the role, believing that the best candidates could be found through our own search process.

We found each of these qualities in Randi Jakubowitz when we first met her back in January of this year. Randi’s track record of building and scaling exceptional teams spoke for itself. She had experience both on the operator and agency sides of talent. She was one of the first HR and recruiting hires at Seamless, where she stayed for 7+ years and saw the company through the Grubhub acquisition and eventual IPO. She played a key role in many of the important management hires that enabled the company to succeed. She was a builder and wasn't afraid to implement processes that had never existed before. While her background checked all the boxes, it was her references that truly set Randi apart from other candidates.

Quite simply, friends, mentors, and managers that had worked with Randi in the past spoke about her in superlatives. Jonathan Zabusky, the former CEO of Seamless and President of Grubhub described her as a “cornerstone” hire in any company. We learned that she thinks like an owner, regardless of role and title, and can lay the foundation upon which to build a highly-successful organization. We look forward to Randi bringing this mindset to 645 Ventures and the portfolio companies that we serve.

Randi has joined 645’s Success Team alongside Guerin Schwarberg, Lexi Quirk, and Stephen Lang. We are incredibly excited to have her onboard, and continue to elevate 645 Ventures as a firm that goes above and beyond for our founders. She has already hit the ground running with several of our portfolio founders, and we are excited to have her on board to reimagine how we support founders with HR operations and top talent recruitment. Please join us in welcoming Randi to the VC community!