Here at Sweep, we're excited to be launching a new interview series highlighting people who said "hell no" to the status quo and established themselves as innovators in the Revenue Operations space. Some of these folks started in RevOps before it was a 'thing.' Others built teams with people from entirely different backgrounds or got creative with limited resources or adopted technology before it became popular. And some simply forged their own path forward.

In this post, we’re excited to feature Kristina Diederich, VP GTM Operations & Enablement at Cloudinary who shares her thoughts on the integration of AI and why she has never accepted the status quo (and never will.)

Sweep: What initially brought you to the world of Revenue Operations?

Kristina Diederich: I was an SDR and had worked with our EVP of Sales on a community relations board. The company I worked for was doing an acquisition that would essentially have us double in size overnight. I was presented with an opportunity to move into a "Sales Financial Analyst" role - doing territory planning, quota / commissions, and of course reporting and forecasting. I basically landed in sales operations just before it became the hot new thing.

Sweep: What is one "out of the box" idea you had while working in RevOps? Was it successful?

Kristina: I don't think I have ever been accused of being "in the box". I've always challenged the status quo. My least favorite answer to "why do we do it this way" is: "because that's the way we have always done it".

I have broken down silos within an organization starting with RevOps, changed how we report on revenue, changed how we forecast, and changed the ICP to help a company grow its revenue.

I guess the most “out of the box” thing I've done is never accepting what was in front of me as the answer or the best way to do something.

broken down silos quote
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Sweep: How would you describe your Revenue Operations philosophy?

Kristina: Progress over perfection. I know when I start any RevOps related project, I'm going to pivot. Multiple times. I rarely end up with a straight line between point A and B, and I have watched some colleagues struggle with getting it to "perfect" before deploying - versus a phased approach, where I know there will be iterations, and feedback, and missteps. Sometimes if you stick to the plan, you miss the outcome.

progress over perfection quote

Sweep: What was one tool or piece of technology you introduced to your team? How did you get buy-in? And what were the results?

Kristina: Well there it depends on the company and where the gaps are. I have joined companies with no commission tool, no CPQ, no forecasting, no account planning - I've seen it all (and survived) - it all depends on the organization and when you're walking in and what the current state is. What's the priorities of the organization...of GTM? I have an ideal tech stack now that I have developed over the years, but there's never been a tool I walk into every organization.

Sweep: What do you think will be the next BIG thing in RevOps?

Kristina: The next big thing? I mean AI will contribute to everything in society from here on out - that's probably just an odd fact of life now. Will it influence RevOps? Absolutely.

I don't think it's a secret that over the last 18 months to 2 years the tech industry has taken a hit. Some GREAT talent has been laid off, companies restructured as they adjusted to market conditions and missing revenue numbers. I think you will see RevOps have to challenge the status quo where you can leverage automation, change sales strategy - pivot how a company goes to market and reset (and manage) expectations of the business.

Sweep: Where do you think RevOps will be in 5 years? And where do you think you’ll be in 5 years?

Kristina: I think RevOps will only continue to grow. I see smaller companies recognizing the need and value of RevOps earlier in their evolution all the time - the need for reporting, forecasting, understanding leading and lagging indicators and being able to pivot a strategy to course correct as the market / economy changes. I think we will continue to see RevOps breaking down silos as companies look toward the customer journey end to end - from acquisition to onboarding and beyond.

As to where I see myself in 5 years? I don't know - at 27, in that same EVP of Sales office that gave me this opportunity - I told him I wanted to be a VP before 40. He laughed and said he didn't hit that till 45. I did it at 37. Next I'll be a CRO - is that in 5 years? I don't know - but I know I'll continue to be a "RevOps Rebel."

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