From Rocket Ships to Revenue: The Career Trajectory of One VP of Sales

Member Spotlight: Matt Kilmartin, VP of Sales, CertifID

Growing up in Australia, Matt Kilmartin kept his eyes fixed on the stars — literally. Once an aspiring rocket scientist, he studied aerospace engineering and business at Royal Melbourne Institute of Technology. But careers often bring us to unpredictable places. After college, Kilmartin landed a job in Detroit in 2011; he traded in spaceships for cars. 

Befitting of a would-be rocket scientist, he was always a numbers guy. Early in his career, Kilmartin worked in a technical sales engineering role. But it was his passion for working with people that helped him change the trajectory of his career and life.

“I spent a few years working in the automotive industry doing technical engineering work, but it just didn’t fulfill me,” he says. “I found that working in the automotive industry was a little bit like an old boys’ club. You had to be there 15 or 20 years before you really got anywhere in your career. I hated that idea. So I actively sought out an environment where I would be amongst peers who are young and driven and ambitious.” 

Making the right moves

His first step was obvious. Get out of the car industry and into technology. He found a “baptism” to a revenue-focused career at Ambassador Software, a MarTech company. After five years, he moved to his current role, VP of Sales at CertifID, a digital platform that prevents wire fraud in real estate transactions.

It isn’t about making a lot of moves to get to a leadership position. It’s about making the right moves. For Kilmartin, that means patience. He strives to project the level-headedness and patience he’s learned the hard way. After Ambassador Software was acquired, Kilmartin quickly discovered there was no use getting frustrated by the change of pace.

“At first, I couldn’t wrap my head around it,” he says. “It felt constricting. Then I got this heavy dose of reality — you’re a 50-employee startup going into a multi-billion dollar company. Some of these executives have been here for decades. They’re not necessarily out to get you; maybe they’re just struggling to understand the way you do business. You have to assume they want to make this relationship work, too. That’s why assuming good intent through any negotiation or pushback is important. That carries over in day-to-day life and the way you communicate with teammates, especially when you don’t get to see them face-to-face all the time.”

Building relationships in a remote work world

Assuming good intent can be difficult. Emails and Slack are cold and impersonal.  Email is a cold way to communicate. You can’t tell if the writer is smiling or frowning. And we could all use a sarcasm font. The high volume of Zoom meetings that have become the reality of the COVID-19 pandemic don’t work as well as an afternoon lunch for building relationships. But Kilmartin and his team have found ways to adapt and manage the shift to remote work. 

“Expectations go up from a communication perspective,” says Kilmartin. “Messaging can get lost in Slack. Setting ground rules as we bring on more people who aren’t in the office has been a big focus for us.”

Kilmartin has learned that relationship-building is key to career success, just like he realized from his time in the auto industry. But as he continued to climb the ladder, he also noticed he started to run out of peers. Who, exactly, do you talk to about making global strategy decisions or when you need career advice from other revenue leaders facing the same challenges? You can get sales tips anywhere, but expert knowledge from like-minded peers is hard to come by. 

Finding community

That’s where Revenue Collective came into play for Kilmartin, and why his debut on The Revenue Collective podcast focused on how to land your first VP of Sales job. 

“As you go up and up, you have fewer peers that have been through similar experiences, especially within the company that you work for,” Kilmartin said. “So there’s no one to lean on and collaborate with. That’s what I looked to Revenue Collective for. I’ve always liked the idea of accountability and being a part of a community like this, where people are driving each other and raising each other up.

“I think that opened my eyes, not just to what I’m getting out of the relationship with Revenue Collective, but to what I can give back to people who are looking to transition to a sales leadership role. What kind of lessons can I pass on from my experience that might help someone get there quicker or more effectively?”

It’s that give-to-get attitude that attracted Kilmartin to Revenue Collective. His appearance on the RC podcast helped him prep for his first VP role, and he hopes it will make others feel like they belong as leaders in companies — with a personal touch, of course.

“Everyone gets that imposter syndrome from time to time, especially as you’re on the upswing of your career,” he says. “I thoroughly appreciate that genuine connection — to be seen as someone that has valuable insight and experience that other people might be able to benefit from.”

2020 Revenue Collective Year In Review (And What’s To Come In 2021)

Friends and fellow Members of Revenue Collective and Operations Collective,

The words we use to describe 2020 have all become a bit trite. Perhaps there aren’t words for the year we’ve all gone through. Yes, unprecedented. Yes, often tragic. Scary. And surreal. And inspiring. And boring. And repetitive. And enclosed. 

And another word: perseverance.

That word, perseverance, is such an important word for all of us. It’s been a year that required it. As I’ve told many friends and colleagues over the past few months, you can ask me about any year in my life and I’ll likely have to look up where I was and go over my calendar to trigger any memories. But the entire world, all of us, will always know where we were in 2020. We’ll remember the people that got sick, the loved ones that passed away, and, just as importantly, the people we helped and who helped us. The people and relationships that helped us get through this year.

I spent most of the year in the same place I’m writing this letter from–my living room in the West Village of Manhattan. I was here in March when the city shut down. And I was here in April as the cases peaked and they converted a tractor-trailer into a cold storage morgue for the hospital nearby. And I was here when my wife came down with COVID in Atlanta while I was trapped in New York and calling into the ICU every day to see how her blood oxygen levels were doing. 

We all have the relationships and rituals that got us through the year. For me, it was my two dogs, Walter and Oscar, whose beds are next to my desk in the living room and who spend most of the day sleeping next to me. It was Monday poker nights and Wednesday Spades nights all over Zoom, and it was talking to my parents every day and making sure they were safe and sound.

And importantly, for me, and for many of us, it was this community. 

Reinvention in the Midst of Crisis

I’m grateful and proud of how Revenue Collective responded to the pandemic and the steps we took to make sure we were there for each other during this crisis. 

In January, we were hosting one webinar every two weeks, we were a team of three people, and the community was just over 1,000 Members. For those in big cities, we would get together for dinners and drinks periodically. For those in small cities, you might not hear from us very often.

Today, and in response to what has happened to the world in 2020, we’ve managed to reinvent Revenue Collective for the new world we inhabit. We are now hosting over 30 digital events each week, all focused on different interests, functions, and needs. We are regularly running benchmarking surveys to give Members actionable data they can use to make better decisions in real-time. We have integrated Guru, a fantastic learning management system, directly into our Slack instance to ensure that any document, template, or event recording is available to Members at the touch of a few keys. 

And, perhaps most importantly, at least for me, and something I’m most proud of, we launched On the Bench. 

On the Bench and the Evolution of Revenue Collective Career Services

On the Bench was our response to the fact that hundreds of our Members lost their job during the pandemic. We wanted to create a space and a community for folks where people could share ideas and insights, receive coaching and access to instructors, mentors, and even recruiters, and mobilize to ensure that our Members were poised and equipped to handle this difficult and unexpected transition. 

As of today, we’ve had over 330 Members pass through our On the Bench community. We’ve helped over 500 Members find jobs in 2020 both through On the Bench and through our other resources. In fact, each week on Revenue Collective we’re sharing close to 50 new roles and have shared over 2,600 open opportunities this year. 

Just over the past few weeks, over 50 Members have left the Bench to find roles. 

I want to personally thank Fred Mather and Caitlan Mackey from Revenue Collective for their passionate leadership of this community over the past year. The heart and soul they put into the community helped our Members and gave them assurance and comfort in truly difficult times.

I also want to thank all of our partners that have helped our Members this past year, notably including Redpoint Ventures, Sequoia Capital, General Atlantic Partners, Daversa Partners, Kindred Partners, True Search, and many more. 

The work that we started in 2020 centering around On the Bench will continue to expand in 2021. We will be building an entire suite of career services focused on providing assistance to people in times of transition and to help access resources and information in times of both stress and opportunity. 

Our First Value: Member Delight

We’ve grown a lot in 2020 as a result of all of this effort. In fact, we’re now over 3,500 Members all over the world. Whether it’s 500, 3,500, or 50,000 Members, I want to reassure and underscore to our Members our mission will always be the same:

To help all of you unlock and achieve your professional potential, whatever that means for you.

In 2021, we have even more planned. Our goal will be to continue to add value to your Membership in ways you’ve thought of and in ways you haven’t. 

As we announced today at our first-ever Annual Kickoff (AKO), we are focused on continuing to invest back into the community across three broad dimensions:

  • Peer-to-Peer Learning and Support
  • Training and Certification
  • Career Services

Each of these areas of focus will expand beyond where we are today to new levels, new resources, and new services on behalf of our Members. 

Peer-to-Peer Learning and Support

In an ever-changing world, one with little stability and unending volatility, the best and most relevant information is often too new to be found in a blog post or a textbook. In fact, it’s often in the minds of practitioners who themselves are only discovering new methods on the fly. 

In 2020, Revenue Collective facilitated almost 700,000 conversations between Members looking for help and support. Importantly, we also worked hard to ensure that when we did find answers we could codify them and make them available instantly to our Members. 

By integrating our community workspace with our learning management partner, Guru, we have been able to categorize and classify close to 1,000 different topics and areas of interest that Members can now access with the click of a button–from data on executive compensation to job descriptions to playbooks to comp plans. This is all available at our Members’ fingertips and all leveraging the expertise of practitioners and peers, delivered and codified at the moment our Members need it.

In 2021, we have more plans to help bring people together. This month, we’ve begun rolling out global Small Councils introducing Members at similar stages of growth and function to help make the global community small and intimate, and to ensure that like-minded peers facing similar challenges can build relationships across borders, across time zones, and across the boundaries that separate us from each other.

We’ll also continue to invest in our private communities for the C-suite. In 2020, we formally launched our private CMO and CRO communities, and in 2021, we’ll expand into new executive-level functions across both Revenue and Operations, ensuring our most experienced Members have the ability to connect directly with like-minded peers. 

And for those who are wondering, assuming that Dr. Fauci and other leading health experts around the world give us the okay, and assuming that attendees can confirm they’ve been vaccinated, we very much do intend to reintroduce in-person gatherings in the second half of the year. 

When we started Revenue Collective (unofficially in 2013, officially in 2016), we were just focused on a small group of operators in New York City. As we’ve expanded into new cities and talked to more executives, it’s become clear that our vision of a world where current and future executives have the resources and support they need to unlock and achieve their professional potential is not limited to customer-facing functions.

Operations Collective, Enterprise Leaders, and New Communities

To that end, in November, we announced the launch of Operations Collective, a new executive community focused on Finance, Legal, and People professionals. Operations Collective will leverage the same infrastructure we’ve used to build Revenue Collective. But, perhaps, more importantly, it will leverage the same values. Those values being a complete and unwavering focus on the success of our Members and an unswerving commitment to building whatever it takes to help our Members reach their goals.

Meanwhile, we’ve also quietly been building a different community, called Enterprise Leaders, focused on revenue executives at the largest of companies. We recognize that the challenges a CRO of a company doing over $1B in revenue faces are different than a CRO at a Series A start-up. To that end, our Enterprise Leaders community is now over 25 Members and features only executives at companies doing more than $1B in revenue. 

If Enterprise Leaders continues to succeed, we anticipate building out new communities focused on executives facing larger and different challenges, again ensuring that within the broader global village of Revenue and Operations Collective, we are doing everything we can to build smaller sub-communities of like-minded and similarly-experienced professionals where trust and intimacy can continue to be fostered.

Training, Skill Development, and Certification

This past Fall, we quietly tested another new concept titled “CRO School.” In CRO School, we gathered 10 of our best and brightest VP-level executives and worked with them over 13 weeks to train them on the skills necessary to become Chief Revenue Officers. We brought in an incredible lineup of guest speakers including folks like Josh Allen, Tomasz Tunguz, Travis Bryant, Adi Dehejia, Fred Mather, and more. 

In 2021, we will be tripling down on training and professional certification for our Members. This month we are launched our first Rising Executive program, a year-long course designed to teach and help Associates take the next step and prepare themselves for the Vice President title. We have over 100 students enrolled in our January class and will be accepting new students on a rolling monthly basis. 

Graduates of both CRO School and Rising Executives will receive official certifications and we’ll make sure all of our talent, executive search partners, and hiring managers are aware of who these special students are–graduates of our programs will have access to the instructors of the program as personalized advisory boards and will have insights and knowledge that will better prepare them for the inevitable step up to the executive ranks. 

Meanwhile, through an incredible partnership we announced today, all Revenue Collective Members will now have access to over 25 different courses, taught by seasoned experts, across sales, marketing, customer success, and operations through Sales Impact Academy. All of these new courses will be included within Revenue Collective Membership. 

We expect these courses to grow from 25 to well over 100 by the end of 2021, making Revenue Collective the pre-eminent platform not just to access ad-hoc peer-to-peer learning, but structured education and professional certification as well. 

Continued Investments in Career Services

As I mentioned above, in 2021 we’ll also be focused on packaging and expanding our various career and job assistance options into one comprehensive department called Career Services. 

Career Services will include all the services we currently offer Members including our On the Bench community for those in transition, access to the ~3,000 jobs that were shared between Members and partners in 2020, and access to 1×1 coaching and mentoring.

But we’re adding much more. 

First, we’ve rebranded our Legal Hotline to a Career Services Hotline expanding beyond simple legal introductions (for when you’re negotiating an offer or you got fired or anything in between) to include introductions to accountants, wealth managers (to ensure you are well-positioned for moments of liquidity), and other career coaches and service providers you might need access to, all vetted and trusted partners. We even have a formal Compensation Coach on staff to help negotiate offers and provide insights to Members on effective strategies.

Second, we’re investing heavily in our new partnership with ScaleWise, focused on helping our Members earn money through their Membership. Through this partnership, we’ll help source consulting, coaching, and advisory opportunities for our Members. Meaning, through your Revenue Collective Membership, you’ll be able to source new revenue while improving and honing your skills as an operator, making you that much more valuable to your current employer.

Finally, we’ll also be packaging the re-launch of a new mentoring platform under Career Services, with the goal of matching over 200 Mentors and Mentees by the end of Q1. Mentorship is a critical component of career development and we’re excited to enable a more effective and scalable solution to help people find relationships they can use to guide them over the course of years. 

The Big Idea: A Career Enablement Platform Serving the Individual

As we’ve grown, we’re often asked, “What’s the big vision for the future?” And when I was first getting together for dinner and drinks with friends in Flatiron in 2013, I can’t say that there was that much of a vision. 

But over the past few months, and in light of everything that’s happened with COVID, the vision has begun to reveal itself. 

We envision a world where executives at every stage of their career, at every type of company, and in every function can use the platform we’ve built and will continue to build to better navigate their career and to achieve professional success.

We envision a world where Membership in our communities definitively and verifiably makes you better as a professional, precisely for all the reasons I’ve listed above. Where employers and investors and partners all are aware of the tremendous resources that have been invested to make Members more effective at their roles and to drive greater impact. 

And, we envision a world where thousands of people come together and agree to abide by a set of standards and a code of conduct, where they agree to give to get, where they agree to be responsive, and where they agree not to spam each other with irrelevant messaging or sales pitches. 

A world where every person that’s a Member of this global pavilion knows that every other Member has been interviewed, has been vetted, and has agreed to uphold a standard of behavior or risk removal from the global community. 

A world where we, as paying customers, are treated as customers. Not as data. Not as inputs to a database. Not because there’s a 3rd party monetization opportunity somewhere else down the line. Not because we’re running a fund on the side. 

A world where each and every one of us gets the personalized human career support we need to achieve our goals.

As we pursue that vision, our sole focus will be on adding as much value to your existing Membership experience as we can. We are going to focus exclusively on helping you achieve your goals and we believe that if we do that, any growth ambitions we have will naturally take place.

But make no mistake, you are our focus. We are building a community, a platform, and a world where executives are no longer left on their own to navigate the ups and downs of life without truly meaningful, authentic, and compassionate support. 

We are going to be there for you. We are going to help you. And we are going to lift you up so you can get where you want to go, make the money you want to make, have the impact you always wanted, and live the life you dreamed of.

Special thanks goes to the large number of partners that have helped us get to this moment including Outreach, Gong, Sendoso, Drift, QuotaPath, 6Sense, InsightSquared, Redpoint Ventures, Sequoia Capital, General Atlantic Partners, Daversa Partners, True Search, Kindred Partners,

And most importantly, thanks to our Members. 

Thank you for everything you’ve done to help us get here over the past year. Thank you for your support, your friendship, and yes, your perseverance.