Skip to content

Employee Spotlight: Cloudinary’s CRO Allison Metcalfe on Her Path and Passion for Helping Women in Tech Succeed

March is Women’s History Month, and today is International Women’s Day! The theme of this year’s event is: “Women who advocate for equity, diversity, and inclusion,” so we’re placing the spotlight on Allison Metcalfe, Cloudinary’s Chief Revenue Officer (CRO). Throughout her career, Allison has been committed to advancing diversity and inclusion and dedicated to championing women in tech. 

Cloudinary’s Director of Communications, Juli Greenwood, sat down with Allison to discuss her career, life/work balance, and some of the challenges she’s had to overcome along the way. 

Can you tell us a bit about yourself and what led you to Cloudinary?

I moved to San Francisco in 2007 after a few years of traveling and teaching English. 2007 was an interesting time here because it was when SaaS was all the rage. SaaS was ubiquitous, and it was an investor’s dream come true: you just sell ‘em once, they renew, and yay hockey stick growth! But very little attention had been paid to the work you have to do to ensure those renewals occur as the spreadsheet demands. Account management had always existed but thinking about business value and adoption and CSAT had not traditionally been a part of the role. That really changed around this time; this is also when Salesforce rebranded Account Management to Customer Success. I joined this game from 2007–2013, when I joined four different companies (including Jigsaw, which was then acquired by Salesforce) to build out this post-sale revenue oriented function. 

LiveRamp became a true rocketship and during my time there I moved from VP of Customer Success to a GM role of an entire business — my CEO-on-training-wheels days. I loved expanding my remit beyond Customer Success; I loved working on net-new logos, PR, and product strategy. After my GM role, I moved into GTM strategy (ops, enablement, strategy) and honed my GTM analytical skills. And after that, I was ready for the next thing: CROing. 

This is my third CRO gig, and I can tell you exactly why I was so excited about Cloudinary:  

  1. The product does what it says it will do, and people like it so much they will use it and buy it themselves. With renewal rates in the 90s, high NPS, a strong PLG motion — these are all incredible signals of a product that meets the mark. It is really hard to sell a product with a bad reputation or difficult brand perception, so this was really exciting to me. 
  2. How much organic growth there has been. And since joining the team, I have only become even more excited by this. We have an incredible amount of good inbound leads as compared to other B2B startups. We see millions of dollars in organic growth because customers love using us and they expand their usage in no small part due to the amazing work of our Customer Success team. Imagine if we could operationalize that even more and hit the gas there? Amazing opportunity. 
  3. The remit. I was super excited to have Marketing under the umbrella; we started with Demand Gen but decided to go all in, and I am thrilled about it. I can’t help but think about things from soup to nuts. I love Marketing and have tremendous reverence for it as a craft — especially as it has become so data driven over the last 10-15 years. I have been preaching and selling new ways of doing marketing in various ways for years; I was pumped to take it “in house.”
  4. The people and culture. This is a really passionate, intellectual, smart, kind, people-first, and ambitious company. Cloudinary is special; I could tell that from the beginning. 
  5. The control we have over our own destiny. The fact is that now more than ever VC-backed companies are really hard. The game of showing a path to growth that is unlikely in exchange for an investment putting you on a never-ending hamster wheel is really tough. I love that we can control our destiny and set our targets as reasonably as we see it — providing a true seat at the table, a true ability to set a fast but attainable pace. That is a really unique opportunity.  

Follow-up question: What challenges have you encountered along the way, and how did you overcome them?

I have encountered more problems and challenges than I could list here. At LiveRamp in particular, we invested heavily in executive coaching. I worked with the same coach for almost 6 years — meeting weekly, working through feedback I was getting, working through challenges I was facing or situations where I was not successful in getting my point of view across; it really helped me. I also invested in training programs wherever offered to me; going through the Multipliers training changed my life and I still flip through the book.  

I understand mentorship is important to you. How have your mentors shaped your life and career path? What’s one piece of advice a mentor gave you, and what advice do you have for younger women just starting out? 

Mentorship is critical but I have never had it formalized. I have tons of mentors and a “personal board of directors” (they don’t know they are on it!) I have cultivated over the years. My favorite piece of advice was to stop apologizing; I had such a nervous tick of apologizing that I had notes in a presentation, apologizing for the most ridiculous things. It made me look weak compared to others and was not necessary. I didn’t even realize I was doing it. It is the number one piece of advice I probably give to other women: you don’t need to apologize. 

For younger women, don’t worry about “finding a mentor.” Don’t ask someone to mentor you.  Instead, just approach people you look up to or respect and ask them if you can ask for some advice. But don’t ask for open-ended feedback; give them a situation where you didn’t like the outcome and tell them what happened and how they might advise you differently. Then you can go back to them for another scenario here and there. Ask specific questions. When I get a very generic “will you mentor me?” I have no idea what to do with that. It makes me anxious because it feels like a big ask versus “can I ask for your advice?” I would love to do that. 

What unique perspectives or skills do women bring to leadership roles and/or tech/SaaS?

I don’t know about SaaS in particular, and I don’t know that I would say women specifically bring something unique to leadership because not all women are the same. I don’t know that I exhibit particular “women” traits all the time. I am not super maternal, I am pretty direct, I can lose my temper and get frustrated, and I have high expectations. I push pretty hard. I ask for things directly. I give my opinion pretty directly too. But I am different (we are all different), and I come from a different point of view. If you have leadership that is all from the same place and same experiences, you lose and you don’t even realize you are losing. So I advocate for diversity in general because mixing it up a bit is what makes magic happen. 

We’re both big fans of Kara Swisher. In an interview about women IT leaders, she said, “Go for the big job, because running the thing matters — more diversity changes the equation and results in better outcomes… More diverse decision-making power will make life better for everyone.” What advice do you have for women in tech going after that big job, where the challenges are often greater and stakes are higher? 

I am indeed a huge Kara Swisher fan. A huge part of my draw to her is her unabashed confidence. You never hear her use common “women” tropes like starting every sentence with an apology or laying a foundation of over-humility (guilty!). She is very “I am smart, I have opinions, I am going to say them… and I am pretty sure I am right.” She doesn’t even say she is “pretty sure.” She is way more confident than that, and I can’t even muster up the will to write “I am right!”

Now, she also admits she is not a great employee; she says this all the time. A workplace requires you to collaborate and advocate for your ideas. She has been in the fortunate position to be able to, and be successful at, just starting her own thing. That is not something everyone can do, for lots and lots of reasons. But what she is absolutely right about, and what I have also found when I started to get closer to the C-suite and/or senior positions, is that no one really knows what they are doing with any absolute certainty. They are just confident and have strong convictions. They are not afraid to make the hard call and deal with it if it is not popular. As I found myself getting more exposure to these senior folks it really dawned on me: Why not me? Why can’t I be there? I don’t think what they think or are doing is anything beyond my capabilities. I am happy to be decisive, and I can deal with being unpopular. I love coaching and building people up and moving careers up and to the right. I can look at data and draw some reasonable insights and conclusions and advocate for and explain them. Do I think I am always right? God no, of course not. But I am willing to be in the arena. Just get in there. Have your numbers right. Have a data-driven reason why you believe what you believe and an action plan. Sign up for goals. Increase your risk tolerance. Take big swings. You don’t get promoted or climb by being overly cautious or overly derisking every decision you make — you just don’t. Accept you will make some mistakes and be prepared to own them; people will respect you for it, assuming you can explain why you did what you did and where you or what went wrong. Just get in there.

If growth is a team sport, how can women leaders better support one another? 

Pulling each other aside to offer encouragement and give feedback, constructive and positive. Give the advice when asked — make time for that. Finally, advocate and promote programs or benefits that are particular to women. When I had my first kid, I was the first person to have a baby in the company and I was put in a server room to pump. That for damn sure did not happen to another woman at that company ever again. I have made dramatic changes to parental leave policies, brought in benefits to allow women to expense shipping breast milk, and advocated for fertility care. These things make a big difference to keeping women in the workforce after babies!

Back to top

Featured Post