Culture Eats Strategy

Not exactly the quote used to describe companies and their future, but it does capture our experience. Culture is the center of everything for a company. If it's wrong, all the funding and brilliant strategy work is wasted.

The culture of a company has to be fit for its purpose. What market is the company in? Who are its competitors? What is their culture? If it's a hard charging industry like chip manufacturing, the culture needs to reflect those realities.

One of our key roles at Vestigo is to help early stage startups establish a fitting culture. We also need to monitor and provide comment on how they are doing vis a vis their cultural alignment. Of course, our own culture at Vestigo is critical to our success. You will see that we are thoughtfully structuring culture building as a firm as you review this issue. Building trust among the team as well as providing feedback and sharing learnings are critical to our success as investors.

We are always interested in your insights and feedback so just let us know what you think about when you contemplate culture. Reach out to mcasady@vestigoventures.com with your feedback.

- Dave & Mark


Envisions Interview

Culture Eats Strategy

w/ Shawna Stewart, VP of People Operations at Railz

Heading people operations at a startup is no easy feat, but Shawna has been a real force multiplier in optimizing success! Tune in to learn Shawna's tips and tricks from day one in the role when she conducted a listening tour surveying employees on what is going well and what are their productivity blockages to breaking down the KPI model she uses to measure progress. These are some of the success tactics Shawna employs to create and maintain Railz's winning startup culture.

Vestigo's Montreal Team Offsite

When I think about those nights in Montreal

... and days too!

Believe it was Gino Vannelli who wrote those timeless words about the wonderful city we visited in July. Montreal is home to several of our venture capital friends who hosted a local start-up fest.

One of the ways we are building culture at Vestigo is by visiting a city for 2-3 days. The goals of our visits are to deepen our connections within the city's FinTech ecosystem as well as to exchange stories as a team and learn more about each other. Often significant others/partners and spouses come along as well. Building relationships in this way has helped us understand perspectives and build trust.

We are sharing scenes from the visit showing our time at Start-Up Fest, visiting fellow VCs, as well as family-style team dinners. All of it in the belief that we learn best by doing and meeting people with entrepreneurial drive and talent.

- Team Vestigo

Mark Casady, Kelly Shaw, Bill McCarran, and Nick Kim engaging at Startup Fest with a note writing exercise
Startup Fest Pitch Competition
Vestigo team + family and friends

Persistance, Tenacity, and Patience

As we discuss the value of culture, I can’t help but think about our portfolio company, Jobble. We led Jobble’s Series A in the summer of 2019 after being introduced to them in January of that year. The Co-founders, Zack and Corey, have known each other since their days at Northeastern University, where they founded Collegiate Contacts, an early iteration of what ultimately became Jobble. They connected college athletes that had spare time with employers that needed some additional bandwidth. They knew there was a better way to connect gig workers and employers that the market was missing. Ultimately, they both went to work for established industry players, and with the experience / knowledge gained they came back together to found Jobble.  

Mid-year 2018 the Jobble business model shifted from purely focusing on the existing (and prospective) Jobblers (fka gigsters) to work with small to large companies to run the entire process for outsourced workers. In the second half of 2018, their top-line revenue grew 5x over the first half of the year. WOW! In addition to the highly successful gig placements and outsourcing they had built a complete value chain for their customers, from the postings to reviews to payroll and they identified the next step on their journey was to offer benefits to Jobblers that were historically reserved for W-2 employees only.  

Inserting a robust Series A in July 2019, they had a healthy war chest to sure up their technology and build a platform capable of handling millions of Jobblers. In turn, they were able to achieve 4x revenue growth year-over-year. Throughout the second half of 2019 the Jobble team grew with many key / senior hires. The most impressive part of their hiring process was the final determining factor, “is this person a good cultural fit?” In the early days of Jobble, Zack and Corey had brought in some incredibly impressive people, based on their resumes. As a result there was meaningful turnover and the success they should have achieved was not materializing. When they shifted away from pedigree decisions to prioritize culture and skills they found their groove.  

This formula for success proved itself out in 2020. After two consecutive years of incredible growth, everyone was ready for an amazing 2020. Going into that year, Jobble had a robust pipeline of customer renewals and a late stage, high confidence sales funnel. Unfortunately, 70% of their sales funnel was events and hospitalities, which essentially disappeared overnight as the reality of COVID set in. Rather than trying to fight the tide or questioning their business, Zack, Corey and the expanded leadership team rallied together and shifted their entire business development efforts on essential industries. The entire team pulled together, worked tirelessly and despite a hundred year headwind they defied all expectations and achieved the original revenue goals for 2020. Again WOW!

When speaking with Zack and Corey about the past two years, this is what they had to say: “As they say, when the going gets tough, the tough get going, and as a team that embraces the “underdog mentality”, we are prepared to overcome whatever challenges the future may bring."

In my experience, Jobble is a shining example of scrappy entrepreneurs that learned from their mistakes, shifted their approach and placed a high value on culture. The investment in culture has paid outsized dividends and their cultural mantra is incredibly succinct “get sh## done!" Not a typical long winded mantra or requiring an explanation, they have a team that trusts each other, they work together towards common goals that are clearly communicated from the top down and throughout the entire company, and in the end they “get sh## done!”  Well done Jobble on the team you have built and the success you are achieving!

- Michael Nugent


Portfolio Updates

Alloy's Latest Post-Valuation at $1.55B!

Alloy has raised an additional $52M at a $1.55B valuation 11 months after raising $100M at a $1.35B valuation. Lightspeed Venture Partners and Avenir Growth co-led Alloy’s latest financing.

Alloy leans on fraud prevention to land new $1.55B valuation
Startup Alloy is on a mission to help banks and fintechs fight fraud while onboarding new customers in the U.S. and abroad.

Vestmark Names Karl Roessner as CEO

Vestmark welcomed Karl Roessner, FinTech industry and E*TRADE veteran, to the leadership team. As CEO, Mr. Roessner will work closely with Mike Blundin, newly named President and COO, to drive the company’s growth and help lead the wealth management industry.

Press & Events
Learn more about our latest press releases and events.

A New Look on Roots Automation's Website

Visitors of Roots' website can now meet their Digital Coworkers by name as well as explore their solutions and case studies.

Roots Automation | AI for Insurance
Free your people of inefficient, repetitive, soul-destroying work with our Digital Coworker. Make work more human.

Interesting Reads

How to Build a Startup Culture That Scales
Like having a strong sales or marketing team, company culture can make or break your startup. As your business grows, learn to build, iterate, and scale its core values.
The Soul of a Start-Up
There’s an essential, intangible something in start-ups—an energy, a soul. It inspires enthusiasm and fosters a sense of deep connection and mutual purpose. While this spirit persists, engagement is high and businesses keep their edge. But all too often, companies lose their souls as they mature. Fi…
Creating The Culture You Want To See In Your Company
Creating the Culture You Want to See in Your Company When Melissa Daimler, an expert on intentionally developing positive and productive company cultures, sat down to write a book on the topic, she had already reviewed every book, article, and research paper she could get her hands on dedicated t…

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