44: Roxanne Pepin: Startups and the ability to learn RevOps

Today we are joined by Roxanne Pepin, she’s currently based out of Spain but works for Rewind– an Ottawa based startup as a Revenue Operations Specialist. She manages all the tech that powers Rewind’s sales, marketing and success teams.

Before carving a niche in operations, Roxanne wore many digital marketing hats working for an SEO agency then a tech company. She’s actually a computer science drop out turned writing grad where she also spent time in content marketing.

More than just a fixer or a troubleshooter, she’s a convergent thinker. Roxanne is described by her peers as a poised and knowledgeable Salesforce admin and a Hubspot platform whiz with a knack for bridging departments together.

Her journey growing into a role at one of the coolest companies in Ottawa is deeply rooted in mastery and pragmatic problem solving.

Roxanne, we’re pumped to finally have you on — thanks for taking the time and chatting with us.

Is being a digital nomad really as good as it looks? 

RP Yes, maybe even better. lol

Remote comms

You’re servicing a team of what 40+ marketing and sales teammates? How do you effectively communicate and collaborate with your team remotely from your spain office? 

RP Honestly, a lot of my role is answering emails and messages, but I find that being six hours ahead and having my mornings free because my team isn’t online yet allows me to hunker down without distractions and get stuff done. Then when people start to come online I have time to focus on them, hop on calls or zoom meetings, and dedicate that time to them. 

Everyone knows my schedule, they know that I’m only online until noon their time so they book meetings or slack message me during that time. As long as we communicate our schedules everything works. 

I try to both remain flexible if there’s something that needs to be done, but also stick to my working hours so that I don’t just have my face buried in my computer at all hours. 

It helps to have people on your team that you trust to do a good job and that you can direct others towards as well. 

How to say no

One of my favorite quotes from a presentation you gave to my students this year while describing your role and journey was:

“everything is doable, but it doesn’t mean you should do it” lol

Maybe walk us through some of the stories behind that mantra and why it might be helpful for other marketers when it comes to prioritization and concentration.Honestly, I’ve seen too many intermediary platform connections fail. 

RP I try to weigh how valuable an automation or a connection will be against how many connections and tools it requires. 

If you’re trying to eliminate three clicks from a process but I need to connect four different platforms to make that happen, I’ll likely say no because the odds of one of those connections failing is high and then we need to do damage control which will take a lot more time than your three clicks, you know? 

One thing that I’ve also learned is that everyone thinks everything they ask for is super important. And sometimes these things are only very important until they forget about them two days later. I once spent a few days connecting things and configuring things, working with a platform’s support team to get a couple reports combined that came from different sources that had very different ways of presenting data because it was vital that we combined these two numbers, but then when it was all said and done, no one cared or used the new report. 

Sometimes if I’m questioning the importance of someone’s ask, I like to let it stew for a couple of days just to determine if it’s really as important now as it was two days ago.

I’ve also come across some things where it was like… “hey can do you automate this repetitive task” OR “can you set up a notification for this thing that happens a lot, I need to know when it happens”. Then a few weeks later I get the “hey, can you turn this off, it’s really annoying” message. 


As someone who works in Ops, you don’t always get the chance to play on the front lines and do customer facing stuff. You often need to also focus on your teammates.

Walk us through how big of a role training and facilitation comes into play in your day to day?

RP Honestly, it’s in my best interest to make sure my team knows how to use the tools at their disposal. 

What good is it to me to set up processes and tools if people don’t know how to use them? Then we end up paying for things we don’t need. 

The other thing is that a big part of ops is to make things as efficient as possible for those customer-facing teams. In the end if I make their jobs easier, they can do more of what they’re meant to do and that leads to more revenue and more growth which is the goal we’re all working towards. 

No barriers 

Something I struggled with when I was in an Ops role was that I didn’t always get to pick projects, I didn’t always get a say in strategy. 

So if you could remove all barriers and constraints, what project or idea would you love to tackle or be known for solving.

RP I love implementation projects. I like new tools and I like setting them up. Which is again another area where I feel like I got super lucky. At the time that I was brought on to the team at Rewind we were looking to implement Hubspot — admittedly this is part of the reason I was hired — so I got to spearhead that project and set up our platform from scratch.

Now that we’re growing and in need of a better sales tool I’m leading a Salesforce implementation project. In the past I’ve been handed over both of these platforms and have had to learn what the heck people did, whether it was done right, how to fix the things that weren’t — and trust me there were a lot of those. So I really like being part of the entire planning and implementation from the start. 

Advice for your past self – What skills would you focus on early in your career?

RP Well.. I learnt pretty much everything I know through doing. I didn’t have marketing training, didn’t have sales or support experience. I went to school for writing and ended up in marketing. So I do think it would have helped to learn more about those aspects right from the start. 

But honestly, I’ve always been a curious person, my mother will reassure you of that. So I don’t really have any regrets or times where I’ve thought “damn, I wish I’d focused on that earlier” because in the end I may not have ended up where I am and I am so so happy to be here. 

Maybe some advice for my past self would be to stop doubting myself. 

We often hear: “fake it ‘till you make it” but I like to think of it more as of “be confident that you can learn what you need to as you go”. 

But be honest and upfront about what you know while reassuring yourself and people around you that you aren’t afraid or willing to really dive in get shit done. 

Why Ops?

We can dive into some of these roles a bit closer but I wanted to start by getting your take on why you gravitate towards Ops? 

RP This is always a funny question for me, because I didn’t really ever think about ending up in an ops role. 

I kind of just started in a specific role, content writing, then broadened my role when I went in-house as a marketing generalist. 

I got to slowly shape my role as we brought more people into the marketing team. I was able to dictate which areas of my job I wanted to keep and which we would hire someone to take responsibility for. 

Which in the end I ended up taking care of all the automation and operations of the marketing team, then got thrown into Salesforce and sales ops when we needed someone to manage it. 

My role kind of shaped itself in that way and honestly I couldn’t be happier with it. I may have been able to get here faster or in a more direct way had I known where I was going with it, but I learnt so much along the way about all the different moving parts of RevOps that I wouldn’t change it if I could. 

Why should everyone be excited about RevOps?

RP Well, one thing that I heard a lot along the way was that “we need to get marketing and sales working together.” I think RevOps is important because that’s really the essence of it. Getting all of our customer-facing teams (this is what I call the ensemble of marketing, sales, and support) working together.

In my experience, no one on either of these teams is going to take that responsibility. Sales wants to do what sales wants to do, marketing and support to. Everyone agrees that we should be aligned, but no one wants to be the one to take charge of it. 

By creating or bringing in RevOps, we designate that as its own role and people are start to realize how beneficial it is. AND you remove the bias that would be there if you gave the responsibility to a member of either of those teams, you know? 

Why ops in startup land? You’ve worked in (at least) two high growth startups. 

RP This is another entirely unintended part of my journey. 

It’s just another example of me landing where I needed to be. Funnily, in university and college I thought to myself “I really want a nice cushy government job.” 

At my last job I realized how untrue that was just because I randomly ended up in a high growth startup and yes, it can be stressful, but you get to do a lot of fun things. I never would have been able to shape my role as I did if I were in a big company or working for the government. 

I liked moving around in my role, I liked building my team, and I like having too much to do in a way. When it comes to work I get bored easily. If I had to do the same thing day after day I’d go crazy. 

Ops lets me be part of a lot of different things and lets me work with a lot of really great people. 

I know I’ll be working with startups for a looong time because of this. I like seeing big ideas come to life and I like even more being able to contribute to them. 

Last question

We always end by asking, aside from eating KPIs for breakfast, what strategies do you take to stay sane and happy while balancing work and your personal life?

RP Having a separate office. Not having slack notifications on my phone. Not sleeping with my phone in my room.

I’ve actually stopped using facebook and instagram for almost a year now. I still have my accounts but rarely log on to them and was surprised to see how little of it I missed. I think it’s been great for my mental health and has allowed me to let go of my devices a bit. 

Catch Roxanne on LinkedIn
Catch Roxanne on Twitter
Check out Rewind’s awesome WP site


Intro music by Wowa via Unminus
Cover art created with help via Undraw

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