Not every leader is created equally. A bad experience with a revenue operations leader might taint your view of the position at all future companies, but that would be a mistake, as CRO Confidential podcast host Sam Blond learned first-hand.
In this week's CRO Confidential episode, Blond talks to one of the best revenue operations leaders on the planet, Cherishma Shah, where she shares insights into the Rev Ops role, why your startup might need one, and how to maximize impact with this powerhouse position.
Shah is the Senior Vice President of Go-To-Market Strategy, Operations, and Enablement at Guild Education and formerly held the same role at Brex, working alongside Blond.
1:40 Intro
2:57 How Rev Ops fills critical gaps in the sales org
4:35 Cherishma's background, how that led to Rev Ops, and what a great Rev Ops candidate looks like
8:45 How to define Rev Ops
12:43 When is the right time to hire dedicated Rev Ops
20:47 More on the ideal candidate profile
24:11 Mistakes Cherisma has seen startups make as they make the first Rev Ops hires or build out the function
28:26 Where should Rev Ops sit within the org
35:07 Biggest opportunities for impact on the business for first hires
38:33 Scaling the Rev Ops org
40:35 How to structure the Rev Ops team and how to measure impact
47:00 Tactical examples of success Cherishma and Sam have seen
Video: https://youtu.be/S5JpOvgNtSY
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How do you win the post-pandemic war for talent? Send your frontline workers to online school. That's the pitch that Rachel Carlson has made – successfully – to big businesses from Chipotle to Disney, Walmart to Waste Management. As co-founder and CEO of Guild Education, Carlson runs a digital platform that enables workers to get degrees and certifications as a free employee benefit. Though virtual schooling for kids is under fire, virtual education for adults has caught on over the last year like never before. To meet the ongoing need for “upskilling” in the modern economy, Carlson says, company-sponsored digital classes should be as ubiquitous as company-sponsored health plans. The ROI, she explains, is astonishingly high.
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Michael Pryor, Co-Founder & CEO @ Trello, now Head of Trello Product with Atlassian following their recent acquisition.
Kolton Andrus is the Founder & CEO @ Gremlin, the failure as a service startup finds weaknesses in your system before they cause problems.
Dylan Serota, Co-Founder and Chief Strategy Officer @ Terminal, the startup that helps you create world-class technical teams through remote operations as a service.
Rachel Carlson, Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow.
Sid Sijbrandi, Founder & CEO @ Gitlab, a single application for the entire software development lifecycle.
Jeppe Rindom is the Founder & CEO @ Pleo, the simple spending solution for your company automating expense reports and simplifying company expenses.
In Today's Episode We Discuss:
How should founders think about the debate between all remote vs part remote teams? How does life and operations change with each? What are the pros and cons? Is it possible to move between the two overtime?
What can one do to maintain culture with remote teams? What processes need to be in place to ensure a cohesive and streamlined communication process? What technical architecture needs to be in place? Where are the breakpoints when it comes to communication? How often does one need to do in person off-sites?
How does being remote or part remote impact fundraising? How do VCs think about this new structure of operations? What is the right way to present it? How does being outside a core tech hub impact one's ability to raise? How should one run a fundraising process if outside a core hub?
How important is it for your team to be near your customers? How does this change according to sector and customer base? How important is it for your team to be near your investors? Does having an exec and sales team in one place and the rest of the team elsewhere work?
Jason Lemkin
Harry Stebbings
SaaStr
Read the full transcript on our blog.
Rachel Carlson is the Co-Founder and CEO @ Guild Education, the leader in education benefits offering the single most scalable solution for preparing the workforce of today for the jobs of tomorrow. To date, Rachel has raised over $71m in funding with Guild from some of the best in venture with the likes of Michael Dearing @ Harrison Metal, Wes Chan @ Felicis, Byron Deeter @ Bessemer, Aileen @ Cowboy Ventures and Scott Raney @ Redpoint, all backing Guild. As for Rachel, prior to Guild, Rachel was the Founder of Student Blueprint, providing students with academic and career planning tools.
In Today's Episode You Will Learn:
1.) How Rachel made her way into the world of startups having started her career in politics and how insights gleaned from politics formed the idea for Guild Education?
2.) Why does Rachel believe that ambitious Mums are the most under-utilized asset in the economy? What are the biggest misconceptions people have about hiring and working with Mums? How can founders really implement practically facilities, tools and an environment where one can be both ambitious personally and professionally?
3.) Before the show, Byron Deeter @ Bessemer said, "Rachel has been among the best at recruiting star execs across their portfolio". What have been Rachel's biggest lessons when it comes to hiring the very best talent? Where do most go wrong? How has her hiring style changed over the years? What are Rachel's favourite questions to ask candidates?
4.) Why does Rachel believe that mission and margin are tightly integrated? How did Rachel acquire Walmart as one of their first clients? What are the positives and negatives of having a client so huge, so early? What advice would Rachel have for other early-stage companies when they have such behemoths as clients in the early days?
5.) Why did Rachel make the move from SF to Colorado? What did Rachel strategically do to ensure the chances of success were higher? How does Rachel feel about keeping leadership teams in SF and then the rest elsewhere? How did the move impact their ability to hire the best talent? How did their move impact their ability to access the best capital? Between customers, capital and employees, who is it most important to be near?
Items Mentioned In Today's Show:
Rachel's Fave Book: To the End of June: The Intimate Life of American Foster Care, Where The Crawdads Sing
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Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
