The Revenue Engine

Creating Meaningful Human Connections to Drive Customer Loyalty with Rebecca Grimes, Chief Revenue Officer at Ruby

March 18, 2022

The Revenue Engine

Each week, Revenue Operations expert Rosalyn Santa Elena shines the spotlight on founders, CEOs, and Revenue Leaders from hyper-growth companies and dives deep into the strategies they implement to drive growth and share their learnings. Rosalyn brings you inspirational stories from revenue generators, innovators and disruptors, as well as Revenue Leaders in sales, marketing, and operations.

The belief that creating meaningful human connections in our technology-focused world builds trust, fosters customer loyalty, and helps our customer win new business.

In this episode of The Revenue Engine Podcast, Rebecca Grimes, the CRO at Ruby, shares how putting the customer at the center of your business helps to drive revenue growth and retention.

Rebecca also shares how she moved from Chief Marketing Officer to Chief Revenue Officer and how that journey has provided end-to-end alignment across the customer lifecycle and how Revenue Operations is the backbone to the GTM organization.


Connect with Rebecca on LinkedIn or at Ruby's website.

Follow Rosalyn on LinkedIn.

The Revenue Engine is powered by

The opinions expressed in this episode are the speaker's own and do not purport to reflect the opinions or views of Sales IQ or any sponsors.

Rebecca Grimes
Chief Revenue Officer, Ruby

[00:00:00] Rosalyn Santa Elena: Welcome to the Revenue Engine podcast. I'm your host, Rosalyn Santa Elena, and I am thrilled to bring you the most inspirational stories from revenue generators, innovators and disruptors, revenue leaders in sales, in marketing, and of course in operations. Together, we will unpack everything that optimizes and powers the revenue engine. Are you ready? Let's get to it.

When I first met Rebecca Grimes, the CRO at Ruby, we connected right away. Our thoughts around the revenue operations function, the revenue operations leader, how the CRO partners with and leverages rev ops, how rev ops supports the end to end customer journey, how rev ops helps enable and drive revenue growth and retention. Everything, everything was aligned, which is one of the reasons I'm thrilled to have Rebecca join me in this episode of the Revenue Engine podcast.

[00:01:09] Sponsor: Today's podcast is sponsored by Outreach is the first and only engagement and intelligence platform built by revenue innovators, for revenue innovators. Outreach allows you to commit to an accurate sales forecast, replace manual processes with real time guidance and unlock actionable customer intelligence that guides you and your team to win more often. Traditional tools don't work in a hybrid sales world. Find out why Outreach is the right solution at

[00:01:47] Rosalyn Santa Elena: Here's a powerful leader who not only understands revenue operations, but understands the end to end go to market motion. The importance of leading with vulnerability and why spending time with your customers is one of the best things you can do to power the revenue engine.

So please take a listen to the insights from this amazing leader and just all around wonderful human being.

So super excited to be here today with Rebecca Grimes, the CRO at Ruby. For anyone not familiar with Ruby, Ruby provides small businesses with the services, products, and analytics they need to manage customer interactions and deliver exceptional experiences. So welcome Rebecca, and thank you so much for joining me.

We met through having a very aligned approach and perspective on revenue operations, probably one of my favorite topics. So I'm very excited to share your story and just learn more about your journey.

[00:02:46] Rebecca Grimes: Thank you for having me Rosalyn and I am so excited to be here.

[00:02:50] Rosalyn Santa Elena: Great. Thank you. So let's, let's just dive right in.

Let's talk a little bit about your journey, you know, the journey that led you to. You know, you've had a long and super impressive career in revenue, number of different companies across different areas of both marketing and across really go to market. So can you share more about your journey and, you know, some of those key milestones that have led you to where you are today?

[00:03:13] Rebecca Grimes: Yeah. You know, one of my first jobs was being part of a proposal team and, you know, go back 25 years where you would respond to these massive RFPs. Hundreds of questions and they had to be answered printed, put in binders and then shipped overnight against a deadline. And it was in that role firsthand that I saw how marketing and storytelling was a critical part of the sales process as I was supporting the sales team directly.

And so when I, you know, when I thought about what was next for me, I knew that I always wanted to, you know, be a leader. And so I followed the traditional marketing journey where I, you know, did PR and analyst relations and internal comms, events and eventually product marketing and growth marketing and that journey led me to just spend a lot of time interacting with customers.

Listening, conducting research, analyzing data so that I could build a better go-to-market strategy for success. And through that time, I also found myself moving into sales leadership after not seeing the scale, that I was confident that we could achieve at a company.

And so I raised my hand and said, I'm going to go figure out what's going on on the other side of the house. And that was really one of the aha moments of my career that changed everything. So, you know, sitting on the receiving end of those leads from marketing, using the pitch decks and materials that I had created in my team for that team just gave me a new perspective on the way that things had to be broken down into pieces for the different buyers and at different stages of the sales process.

And it also just gave me this like new perspective on the importance of aligned KPIs. You know, from the surface, it looked like marketing was delivering these quality leads, but in reality that our scoring model was just not right. And we had been prematurely sending leads over that still needed to be nurtured.

And educated by marketing before sales engaged in that conversation. And so from that point forward, I just committed that I wanted to be part of a company that aligned my KPIs in lockstep with the revenue organization regardless if I was owning sales or marketing.

[00:05:24] Rosalyn Santa Elena: That's great. That's great. Yeah. I'd love that. And it's interesting kind of when you see the sales team actually pitching the content that you created, the messaging that you created and being able to be on the other side. So you joined Ruby over two years ago as the chief marketing officer, and then after about a year or so then you, you assumed kind of the full picture, right?

The chief revenue officer role, really overseeing end to end go to market right across the entire customer life cycle. And we're seeing. You know, we're seeing more and more, I think CRS rise from the sales leader role, but also more and more coming from the marketing side. So how did that move maybe from CMO to CRO come about?

And what do you see as some of the primary benefits of moving from marketing versus moving from sales?

[00:06:11] Rebecca Grimes: Yeah. You know, there's obviously been a lot of buzz about, you know, is this CMO the new CRO. And even the new CEO? I'm not sure that that's a fit for everyone. Who's a marketer and everyone who's a sales leader.

And so, you know, when I joined Ruby, I was leading partnership sales, marketing, and. The operations function, which we then would rename to be revenue operations. And then about a year later, when I assumed the CRO role, we aligned customer success. And I think that that sometimes is an overlooked piece of the revenue picture.

When you think about. You know, it is cheaper to retain a customer than it is to go find a new one. And so when we aligned under a single revenue team that just allowed us to further break down all of the walls that are between the teams and align around shared retention and growth and expansion targets with accountabilities, with each functional leader.

So it didn't. Replace the need to have functional expertise over sales and marketing and partnerships and customer success. But aligning this revenue team under a single umbrella, supported by revenue operations, to look holistically at the entire customer journey from lead acquisition all the way through.

Sales and onboarding and ongoing support and service and success and retention that gave us a new perspective on the way that we needed to be collaborating, leaning into automation. We were making decisions to support one functional group of the business, as opposed to seeing the applicability as how that technology might solve problems on another team.

Responsibility. And so, you know, really breaking all of that down by aligning this team and then, you know, really celebrating wins or misses together as a team. So there is no marketing crushed it and sales missed the number like that. Isn't a thing that we do, and it is a thing that I've been a part of at other organizations, you know, marketing.

You know, isn't just about lead generation and just doesn't service the sales organization and getting the leads over to them, the responsibility there around brand and supporting internal branding and, and an employer brand, like everything that goes into. Really aligning a team for growth starts with everybody understanding their accountabilities, but also understanding their dependencies on each other.

And so once we, once we came together as a team that provided the clarity that I think that we all needed around, let's go get to work and build a successful operating organization. And you know, we had, we had never really thought about. The journey as a, a full, linear, big picture. Like we would break down, like, this is how the lead moves through the funnel.

And then this is how it moves through the sales funnel. And that's traditionally how it's been looked at it. And most of my, you know, career in in, you know, go to market leadership is really breaking it down into those pieces. But then. Pushing all of those pieces together and saying, oh, that's a little wonky of an experience of a handoff between these two between these two teams, you know, and then, and then understanding the KPIs that aligned to that so that there can be accountability at each stage of that process that, that matters regardless of, you know, where you're at in that funnel, it matters to pay attention to those details and make sure, you know, the buyer.

And your customers don't care who on the other end is accountable for getting them successively to an outcome with your business. So why should we over index on how we organize ourselves and make that more difficult for for a customer to buy from you and to go through at their pace, that consideration all the way through, you know, obviously a sale and then ongoing success with your organization.

And let me, let me just be super clear. I want to come back full circle. None of this would happen if we didn't have. Like phenomenal leaders with deep expertise in each one of those functional areas of the revenue funnel that are now coming together and aligning around strategy and execution. You know, it really is a matter of making sure you're investing in people and knowing when and how to have.

Experts versus generalists. When you're trying to scale a business, I think, you know, we're expected to wear a lot of hats and that's why sometimes see marketing, you know, sales can just do marketing too, because it's just about demand gen and it isn't, it's product marketing, it's understanding competitive landscape and customer sentiment and customer marketing and cogs P is everything.

And when it. When, you know, in my experience I've seen when sales is leading, that it's sometimes forgets the importance of how all of those things contribute to the growth of an organization.

[00:10:59] Rosalyn Santa Elena: Yup. Yup. Oh my gosh. You were like, just speaking, like my language. You're like the like music to my ears, talking about alignment and customer journey and handoffs and just all of this just completely like in my rev ops, you know, in my rev ops world.

It's music to my ears. Thank you for sharing that. I love that. And I do totally agree. I mean, there's so much more to marketing. It's not just about filling the funnel. It's not just about demand gen, right? There's so much more there. So let's switch gears and talk about Ruby a little bit more, you know, Ruby started you know, back in the early two thousands, you know, as a small business dedicated to helping other small businesses, right?

From the founder story, I saw that the business was built on the, you know, and I quote, belief that creating meaningful. Human connections in our technology focused world builds trust, fosters customer loyalty and helps our customers win new business. And I love that. And that's totally aligned with what you were talking about in terms of being customer focused.

So from your perspective, you know, how do these beliefs come into play in your revenue model and really help to acquire net new revenue?

[00:12:04] Rebecca Grimes: Yeah. Yeah. I have always been customer obsessed. And when I first learned about Ruby, I could immediately relate to the value. That the company provided to small businesses also could very, very easily see the full journey and how those teams needed to align around our single vision of delivering those exceptional experiences to build customer loyalty and empower them to freely pursue their purpose.

So when I think about, you know, why we were coming together as a revenue team, the thing that was keeping me up at night wasn't how do we. Grow this business faster. It was, there are small businesses that need Ruby that don't know about us. And our job is to make sure that we help them understand the value that we can deliver to them while also balancing that with our growth goals.

And so I think, you know, it is really important, I think for organizations to believe in their vision, their mission and their values. And we had just went through an exercise over this last year to refine our vision and mission, to make sure that. It included the. The things that mattered the most to us, like cultivating diverse and thriving, local economies and the responsibility that we see in helping these communities grow.

And you know, it, you know, it's no surprise that, you know, there are 30 million small businesses and 96% of, you know, us private companies are. Are creating the jobs in our communities. 64% of every job is created by a small business. And so everyone at Ruby feels so deeply connected to small businesses.

And I think that that comes to life and our content in our sales process, in the, you know, the way that we balance, making sure that, you know, there, the hesitation is confidently overcame through demonstrable examples of how we will. Take that, that brand trust, we answer the phones for small businesses in a very chameleon-like ways.

So you do not know that you are talking. To one of our receptionist or you know, we also support chat interactions on websites. And so you believe you're talking about small business. And so you're representing their brand and for small business, that is everything to them, their brand, their reputation matters, but they also know that that's a missed opportunity for them to.

Potentially acquire a new customer or retain a customer or service a customer by missing that call or that chat interaction on a website or not even having chat on their website at all. And so you know, I, I like, I, I deeply connected to the work that we were doing and. I had felt connected to the work I was doing at other organizations, but not in the way where I could very quickly get this feedback loop where a customer could call us today.

And immediately tomorrow start feeling the impact of our value and breathe a sigh of relief. Overwhelmingly the sentiment is I wish I had found you sooner. And that's the thing that keeps me up at night and how it comes kind of full circle as to when we think about our revenue model. We know that the Tam is there.

We know that the need is there. The challenge. Just, you know, deciphering through the noise of, you know, what actually are the business needs at what stage of growth and how we overcome that that huge leap of faith that small businesses have to take when they're making decisions on who to spend.

Their dollars with. And so it helps in everything that we think about both from the products that we consider, you know, investing in to the partnerships that we curate to better support our, our, you know, new and existing customers, but also just in the way that we think about expanding our services to meet their needs.

It's all with a very central focused on our core beliefs, around our mission and vision. That's our, our calibration layer. When we make these changes.

[00:16:01] Rosalyn Santa Elena: Oh, I love that. I love that. Thank you for sharing all of that. I could just see your passion, you know, you could feel the passion I'm getting excited about, about the product and the offering too, and just the, just the energy, right.

And just the impact that you're really having on these small businesses and people's lives. Right. It's just an incredible When you talk about customers, you talk about customer value quite a bit. So, you know, what are you seeing? You know, some of the things that, you know, maybe you see companies that are, that they're doing really right when it comes to driving customer value.

And, you know, because it's not only about retaining customers, but it's also about expanding, right, expanding into your existing install base. So what are some of those things that you think customers are doing right or businesses are doing right?

[00:16:45] Rebecca Grimes: That, that is such a great question. And I often try to relate my work to the things that impact me as a, as a consumer buyers have options. It's more than just a product or service that people are buying these days. Like there is so much competition and there are so many choices that consumers and buyers have that, you know, customer value has to be considered both as the buyer, but also as the brand that is trying to connect with that buyer, you know, Beyond this, did I get what I pay for mentality?

And it's really shifted to do, do I align my values? Do I believe that this company is being sincere? Are they going to be around. Two years if I buy an HVHC system that has a warranty to come out and make sure that I'm getting what they are promising or committing as part of the total experience of buying.

And so, you know, I think that the shift for buyers has, has really shifted to quality and it isn't just. About the product it's about the service and the support and the, you know, the ad-ons that are available to solve a particular problem that you either have today or may have in the future. And, you know, really, you know, at the forefront of that is expectation management.

I am a big believer that companies are doing really well are finding that they are retaining more customers and increasing their average sales per customer when they are managing expectations, even in this. Crazy challenging world where you're on hold. I, you know, I called to get a detailed receipt from a hotel and I was on hold for like 90 minutes.

And I was like, oh my God, I don't know why I can't get this online in a self-service way. And I'm sitting in a and you know, and, and so when I think about customer or companies that are getting it really right I Kia I live down in the. Like literally a mile away from me is Ikea. And I bought things for my household throughout the years, they have a generous return policy, their support, their support model offers many options.

They manage expectations throughout every interaction with them. I had a piece of furniture for five years and one of the legs broke and it was just continued and they helped me track down a lake. So that I could, you know, not have to go buy a new piece of furniture. But they've been challenged with keeping products in stock.

Like everybody on the planet is struggling with with shipping delays and consumer demand and production. And in December I designed my closet. They have a beautiful, you UX to go in. You put your design, it it's phenomenal. If you're looking for a new closet, you should go check them out. However, for two months, Two months.

They have been out of stock. All of the things that I designed in my closet, and I have been patiently waiting because their value mean something. I could have gone out to another company and I could have replicated the same thing and I could probably already have my brand new dream closet already built out by.

I, I value the relationship that I have with them as a brand and their managing expectations. I've now been texted great news. So they gave me that option. We can text you when this is about to come yes. Deliver on the channel of which I preferred. I would send it in email. I am a chat person. So thank you for offering that as a text option for me.

And And they've told me when it's going to be back in stock. And so, you know, it is that extra consideration that they put in the value of our relationship buyer and, you know, and, and, and brand is why. And that's why I stay loyal to them as a brand. And I think that we all have examples of how we work through the bumps of a relationship with a brand because of the trust that they've either established or like directly established or that they've established for other people that you believe in that.

And those aren't just reviews that don't matter to you. So I think that that is where companies are also falling short is really not managing expectation. Well, leaving people. Hanging on, like, are you actually going to fulfill the thing that I need you to do for me? And when will you fulfill that?

I've heard like horror stories of people buying furniture for their homes and it's 18 months later and they still don't have their new couch and have they known 18 months ago that they weren't going to get a new pouch. They probably wouldn't have made the decisions that they made about. Remodeling everything except waiting for this beautiful or whatever decisions that they made.

And so, like, I just, I, I think that companies that do this well, you are going to see them growing and and the loyalty and the referral and everything that comes with companies that get it right.

[00:21:37] Rosalyn Santa Elena: Yeah. Yeah. I love that. That's a great example too. It's a very good example. So let's talk about employee engagement because I know employee engagement, you know, building a winning team is always top of mind for you.

You talk about leading with vulnerability and communicating frequently and authentically. Can you share more about your approach to leadership and maybe some of the key things you think about to be a strong and effective leader?

[00:22:02] Rebecca Grimes: Yep. You know, my approach to leadership is pretty simple. I treat others as I would expect to be treated and You know, when I think about what that means to me you know, it is leading with open communication and transparency which for me then personally means I have to be vulnerable and share where we're at.

What we're building and the why behind it, which I think is like a critical step that people often miss, because they might think it's not relevant. The why is almost the most important part of leadership is communicating the why behind an ask so that they start to connect the dots in a very meaningful way to understand where they fit.

And the overall objective that you're trying to accomplish. And so it is very easy in a, in a tactical leadership way to just, I need everybody to go do a bunch of things, but when you don't come together under a bigger purpose around the Y you, you have people that, you know, potentially don't believe in the plan, you have potential for folks to.

Miss deadlines or not understand the domino effect of you know, not getting the business requirements right. Or or reprioritizing something different because you're clicking off quick wins, but not tackling the big stuff. And so I really believe that, you know, it starts with making sure that everybody is aligned around a plan.

And where they fit into helping achieve that plan. And essentially when together you know, as I think about the last two years in particular, it's really pushed many leaders to evaluate their management style and try to maintain the right balance of needing, to kind of prioritize the goals of the business with the reality that you know, many people are facing.

A lot of personal struggles throughout the pandemic. You know, obviously in the beginning there was so much fear and uncertainty and that really never went away. I don't, I don't know that everybody has perfectly landed on the solid ground that we all thought that we would be in two plus years later.

And I think it just really shaped, shifted into other insecurities and challenges for our people. You know, if I stepped beyond those past two years, it really. It's about being cute. Like when you, when you are a leader that just is human you're approachable. People don't feel intimidated by you. The feedback loop is more open and honest and it is okay for you to even say in front of your team.

I don't have all the answers and I need you to help me figure this out together. And I don't think a lot of these. Feel comfortable saying that I feel that they see that as a, as a sign of weakness when leading a team. And I actually think it's the exact opposite. I am not the best at everything I am accountable for, but I am surrounded with exceptional people who are, and by me, assuming that I could do their job.

And do their jobs better than them. That, that just like falls in the face of lack of, you know, really true leadership and my opinion. You know, it, isn't just, I meet weekly with my team and do one-on-ones and I focus on development on an annual basis. We do these annual on a performance review. Like that.

Isn't what it is about. Like it just, it's it say are people. Expect more and we owe them more as leaders. We owe them, pushing them out of their comfort zones, not promoting for passage of time, but promoting based on potential and actually growing and and delivering business results that matter you know, conducting skip levels and actively listening, like listening more than you are talking.

Not just going through the motions, but authentically. When you hear feedback and it's something that you can take. Action. Yeah. Take that action and thank them and give them a credit and acknowledgement for that idea. It's hard. It takes time, but the impact of this work is really far reaching. And I think that there are phenomenal leaders that I have seen do this firsthand and the growth of the business and the caliber of the team.

And the potential and the talent rises with that investment when you make it. And so I'm, I'm just a big believer that you have to carve out the time to do this work. And oftentimes it is. The thing that falls to the bottom of the list or the thing that I can punt on to the following week, because I've got all these other bigger things I've got to tackle and you're just kicking the can down the road.

If you're not really making sure that people are in the right role and their obstacles are not in their way for them to achieve individual success.

[00:26:44] Rosalyn Santa Elena: Yes. A hundred percent, 100%. I completely completely agree.

Specific, I guess maybe to the revenue team. Let's talk a little bit about that. Do you have any tips or maybe advice for other revenue leaders on how to keep those teams engaged and motivated, especially in the environment that we're in?

[00:27:07] Rebecca Grimes: Yeah. You know it's so funny because. If I rewind the time 10 years ago, you know, at this time of year, we would have already built the full plan for the year.

We would have it broken down into quarterly themes and we would have hiring plan done. We would have everything really mapped out for the entire year and we would just be marching and pacing against that original plan that we had sent out. And I don't think that works anymore. I think that. Revenue leaders need a plan for headwinds and the abs of flow that happen when you're trying to scale and grow a business.

Like once you figure out how to do something, a wrench is going to be thrown in the mix. You know, whether that's a new market entry or a softening of the market with one specific vertical or a channel, that's no longer performing as expected. And you actually need to be agile and planning for how you weather that storm with your team.

And that really starts with being comfortable with being in a constant state of potential change and, and literally encouraging testing and learning and failing and doubling down on things that are working and diversifying your growth strategies so that you are not dependent on something that might.

Kill your entire plan for the year, because you put all of your eggs in one basket. And again, I know that none of this sounds like, oh my gosh, that's so breakthrough, but there are the rigidity that I think I've experienced previously in my career and the way that. You know, I, I would not be comfortable going and saying, I know I presented this plan to you, but the second half of the year, I think we've actually got to change it up, but we have to go do this.

And this new partnership has a lot of interest. And I think that we, if we were to make this investment in technology and yeah, I know that roadmaps already locked for the next 18 months, but I really think that we need to consider that one thing that has Ms. What that ROI could look like on that. The plan is only as good as the execution that sits behind it with the plan B and C, that also could be pivoted to if plan a doesn't work out.

And I, you know, I think that, I think that that is where. I really see like a permanent change in the way that we need to think about what growth looks like. It is not always going to go as expected, no matter what plan you devise at the beginning of the year, there is going to be something that you did not anticipate that is going to change your trajectory of growth or your retention of your customer base and a new competitor leapfrogs you in functionality.

And. You don't, you had no idea that was coming and it takes a chunk of your existing customer base out. Like you can't anticipate everything at all the same time and keep up with that. And so, you know, honestly, where I lay the confidence in the plan with is, is really backbone. I know you're going to love this.

I revenue operations like that is where we talk about closing the gap on this is what is known in front of us to be our controllables. These are the things that are not controllable that we need to figure out a plan to smooth this out. You know, if you don't have visibility into all of your data, How are you making data-driven decisions and being agile to drive the business?

And you know, it, it really it really starts, you know, with, you know, again, going back to transparency, this is what we're doing. This is why we're doing it. Are you along for the ride? Great. You're along for the ride now. How you bring everybody. And that's the, the second part of your question around engagement.

Like that is really hard because engagement means something different to everyone. You know, some folks think of engagement as like, I want to have friends at work. I want social time together. Others view engagement as I want to be heard and considered. And I want to deeply feel value and know that the work I'm doing means something.

And you know, and then others want to feel connected to the mission and the vision and the work that you're doing at, you know, at, at, you know, the, the macro level. And so, you know, you have to do all of the things in order to bring everyone along for the ride and you also need to be. Really thoughtfully thinking about how you cater to keeping employee engagement top of mind for each one of the individuals on your team.

So it's almost like understanding what their love languages to keep them engaged and wanting to. You know, grinding it, it is hard, right? This is, this is not been easy for anybody to navigate this. And people are starting jobs where they, you know, have never, and potentially will never meet their colleagues in person or their leadership team directly.

And so you know, th the Y coming back full circle to the why behind the work that you're doing and carrying that down to every single person in your team, Is how you drive that engagement and they feel connected and it's okay. Because some people are going to say, actually, I don't feel as connected as you do.

And that's okay too. You know, and creating the space for those conversations with no surprises to happen. Like, honestly, that's an okay conversation to have. And so. You know, engagement, isn't just an annual survey. It's an ongoing conversation and it is something it, you know, we just went through our engagement surveys that we're going through the results right now and building action plans.

And then we're going to drive accountability against all of us to make sure that we are actually delivering. On the things that matter to our people and that varies by team and even to the individual.

[00:32:34] Rosalyn Santa Elena: That's right. I love that. You touched on the fact that, you know, everybody, what, what drives everybody in what they define as engagement and what motivates them, right.

What do they value is different. And as a leader, you have to tailor that individual approach to each person on your team. All right. Let's talk about another one of our top, one of our favorite topics, or maybe not. Some point and hopefully in the very near future, I hope that this topic is not even relevant, right.

Unfortunately though, in today's world sales is still a male dominated field. I think when we look across revenue, it's a little more diverse, but if you look at sales specifically, right. And I think, especially as you look at sales, leadership roles, you see less female leaders. And as a rev ops leader, you know, myself, there's been many times when I'm the only woman in the.

As a woman in a CR role role, right. At a technology company, you know, what advice do you have, I guess, for other women who are really looking to elevate their career and continue to move up that ladder?

[00:33:32] Rebecca Grimes: Gosh, I just spent the better part of January having this conversation with nearly 30 strangers. I went on LinkedIn and I forgot my time.

And I said, here are 45 minute blocks. We could chat about what the next chapter could be. Or you want resume or, you know, advice navigating or promotion within your company. I opened it up. I talked to 30 women in counting, mostly overwhelmingly women. And it bled into February because there just for too many people that I wanted to chat with, and what I overwhelmingly heard from those conversations is that imposter syndrome is real and we just, aren't doing a great job of building up the female future leaders to reach beyond their dreams.

I, I believe we need to be the examples loud examples of how to break down the walls to open doors. And we need to be the ones breaking down the doors for the next generation of leaders. I think that means encouraging people who never dreamed of being leaders to consider it and create those opportunities for them.

That means leaning on our networks more now than ever to help these talented women understand their value and how to find a company who appreciates that value and wants to invest in their future. You know, when I first entered tech, about 20 years ago, I was incredibly intimidated. I was like, oh, what?

Like, no, I don't know how to do any of that. What are you talking? I don't, that's super scary to me. And it can be for a young professional. Right. It feels intimidating. But I had a mentor that said, it's not as scary as you think I will help you navigate this. And I will teach you how to pivot what you're already doing into tech.

And he brought me onto his team and did Justin. And like, I'm so thankful and fortunate that I had that so early in my career, but I also can appreciate how rare that is. I think women need to find a hype person, like someone who is like the counterbalance to those voices of self doubt that creep up on you.

That just knock you out of that Headspace. And if you don't have one, you need to be your own hype person. Yeah. You know, and if any of your listeners need a high person, I'm here, I'm not doing it for the 30 people. The strangers that I've met over the course of January, and they're continuing to engage with me and I have this conversation and this is what happened and what you think I should do next.

Like it, you know, it doesn't have to be a formal coach or, you know, career coach or mentor. Like you just need people that have been in your shoes before and you need to you need to build enough confidence to make sure that. Are going for that promotion. You're asking for that seat at the table. You are and also, you know, in particular, when it comes to kind of revenue, accountable teams finding the high potential and giving them that boost of confidence, that they never considered that that was a path for them.

And I think that, that, you know, if you had asked me 25 years ago, if I was going to end up running an entire revenue team, I would have said, no, I went to, this is not what I went to school for. I don't have those skills. But I've had people that have taught me and, and through the years, you know, I have.

That on myself. And I don't know that everybody takes those chances and, you know, there's, there's some silly statistic about how many boxes when you look at a job description that you need to check in order to confidently apply for the job and go for it. And I know from my own personal experience that if I didn't meet like 90% of the boxes.

I didn't do it. I didn't go for it. And like that bums me out because I'm like, that's how growth happens is you. I can, I can learn anything. I can research anything. I can figure things out. We don't, we don't take that leap. We don't bet on ourselves. And I think that we need to change that culture. And that starts with us being loud about change, needs to happen and making sure that the companies, that we're a part of prioritize that work.

And it's beyond just female leadership. It is representation across the board and it starts with us prioritizing that as an organization and not. To check a box, but because it becomes part of the fabric of the work that we are accountable for doing so. Yeah.

[00:37:45] Rosalyn Santa Elena: That's amazing. I love that. I had no idea you had that many conversations or you opened yourself up for that, but that's amazing. I'm sure.

[00:37:52] Rebecca Grimes: I, I love it. I love it, honestly.

[00:37:55] Rosalyn Santa Elena: Yeah, it's amazing. I know. I think once you get to sort of at a certain part in your career? I definitely think that that giving back and just helping others is the most rewarding. At least for me, it's been, it sounds like it is for you too. It's really impactful.

And just so, so incredibly rewarding. And it does take a lot of time, but it's so rewarding.

[00:38:13] Rebecca Grimes: I, I, I can't, you know, I would not be where I'm at today had I not had people that were pushing me and helping me. And and that I do not take that for granted. I also know that that is. Common. And it is even more common you know, for women to not have that person in their life that is pushing them and shepherding them through their careers.

And so to your point, I feel blessed and I want to make sure that I am paying that forward because honestly I'm excited about the future of our leaders. Like there is, there's a lot of good happening and it starts with that. Helping open those doors for them.

[00:38:50] Rosalyn Santa Elena: Yep. Yep. Love that. Thank you. All right. Let's pivot a bit to operations. As you know, I've been on my soap box, right? For the last few years, really promoting revenue operations. I'm always talking about the function, the people. So this conversation has like thoroughly engaged, like has energized me because you get it right. And I think, you know, selfishly, I always think of revenue operations as.

Especially that rev ops leader, right. That partner is that powerful kind of secret weapon for the revenue team and the CRO. So what are your thoughts on how the CRO can best leverage the ops function to really help enable and optimize the revenue team?

[00:39:27] Rebecca Grimes: You know, at Ruby, the revenue operations team is really the backbone of our, our revenue team and.

You know, the biggest backlog, unfortunately, because of that then with the rev ops team, right? I mean, that's hard like when she was established and formalize this as your partner you know, the function as your partner, it, it then, you know, creates an excessive amount of need and demands on that team.

And so, you know, when, when we talk about the foundational elements that required, you know, You know, scale, this was the team that had to make that happen. You know, we overhauled most of our technology processes, automation, the way that we use data to forecast our new revenue growth and our retention efforts.

And we're still, you know, still chipping away and defining that potential. And, you know, honestly, data's at the center of everything that we do. And the funny thing about data, and I'm sure you get this all the time is like, once you see one piece of data, it's like, I have five more questions about that data.

And like, data is never done. There is never like, oh, here's the big dashboard of how I run the revenue team. I, every day I'm like, oh, what is that over there? That's interesting. Can I dig more into that? And I'm sure my revenue ops team loves that that that's most of our conversations that we have, cause they're like, wow, I got these 15 other things I'm working out and you wouldn't see that.

Oh, my gosh, like there's something there, but you know, when I, when I, you know, think about like that customer journey that we defined, you know, as this is the way that, you know, we've broken down all of these silos and one to interact and engage with our customer base you know, you need that team to bring that to reality, right?

Like you need all of this. Things to be timestamped and logged and reported on, and the automation to work as expected, not just in the form of, you know, the steps of a process, but the creation of tasks based on actions that have happened. Like all of that magic. It is put a lot of demand on the rev ops function.

And, and, you know, when I you know, started looking at the 20, 22 hiring pan, like for the team, like who are the real, you know, folks that we need to add to augment the work that we're doing we're doubling the size of our revenue operations team this year, because we need to invest in that team. And I think, you know, a lot of, a lot of folks are having that, that moment.

And, you know, unfortunately there's also. Scrambling for that talent at the same time, which is making it harder to build out these functions. And I think, you know, our job is to also look at high potential folks that might not check all of the boxes and turn them into rev ops professionals. You do not, you do not need.

Be a master of everything to have potential to deliver in a rev ops role. And I think like, that's how we're going to continue to build out this. This discipline is, you know, you need curiosity, you know, some technical acumen and active listening skills. And like, if, if you, if you have that in your organization and you're not eyeing people that might be able to pivot and make a move into rev ops, if you're expecting to go find all of this talent outside of.

Bring them into your team and have them make an immediate impact as they learn your business and your systems and your tools and your processes. Like that's a really hard thing to move the needle on. And so. You know, rev ops I, you and I could have and could keep talking about the impact of this role.

But some organizations are like, I have a couple of operations and they run our Salesforce and our HubSpot, they run our tab. I have some dashboards and that isn't. That will not be the way that winning businesses scale. It is the same thing. You know, as we talked about marketing, like revenue operations is complex and layered and requires a real passion for understanding the levers available to help drive retention and expansion.

And. And, and in service to the rest of the revenue team and when, when you get that right, magic happens. But also on the flip side, the demands increase on that team. And then prioritization, you know, is something that we're constantly obviously struggling with because, you know, once you open those flood gates, it's like, wait, what you're available to help me these are the 500 other things I need to get done. So.

[00:43:54] Rosalyn Santa Elena: That's right. That's right I love that. Thank you. Thank you. Okay. So as I think about the revenue engine, I think about this podcast, I'm always hoping that others will be able to really learn how to accelerate revenue growth and power the revenue engine. So if there was one piece of advice that you would give to another revenue leader, or maybe another CRO, you know, so that one thing that really makes all the difference, what would that be?

[00:44:19] Rebecca Grimes: Spend time with your customers.

[00:44:20] Rosalyn Santa Elena: Yeah.

[00:44:21] Rebecca Grimes: We make a lot of assumptions. I'm, you know, pragmatic marketing trained and you know, there's the concept of inside out versus outside in approach, the way that you build a go to market strategy. And I still think that. I could talk to our customers every single day.

I never get enough of it. And so if you know, your teams need to be talking to your customers and your customers that leave you, it isn't just your happy customers. It's the folks that no longer use your services or the folks that chose to go to another company and not yours. And so, you know, really making sure that with a lens of understanding the problems that you are solving for your buyers and the segments, and staying on top of the voice of the customer and curating environments for that consistent feedback loop to be shared and measuring customer satisfaction and NPS, as part of that consideration is really.

It's really something that, you know, it isn't set in, forget it is a constant evolution. And if we learned anything about the last two years, the customers, and in particular, our, our small business customers have had to pivot on everything that they knew how to do to run their business. I am a lawyer.

I have a law office. Wait, I don't have a law office anymore. I've got to figure out how to do all of this from home. Why do I even need that space? Any like everything. It's changed for a lot of businesses and their customers over the last two years. And and the only way that we're going to continue to evolve to meet those needs is by listening and calibrating ideas that you have, and making sure that you are building things that actually deliver value and that customers are willing to pay for.

And scrapping something. If you go down the wrong path or doubling down on something, if you see that there is a market need and you have to figure out how to move faster to meet that market need before somebody else does. And so I cannot stress enough. Spend time with customers, read sentiment reviews.

Dig into the data around what is happening with your churn. Spend the time there, as you're thinking about scaling a business, because you, as we said at the beginning, it is much easier to retain customers than it is to replace them. And it starts with just understanding what's happening and trying to make sure that you are sincerely listening and meeting their needs.

[00:46:44] Rosalyn Santa Elena: I love that. I love that. Thank you Rebecca so much for joining me. You've shared so much and everything that you've said to me, I'm just like music like I said, music to my ears. Definitely definitely resonates with me as well.

So, you know, before we wrap up, you know, before I let you go, I always ask two things. Right?

One is what is the one thing about Rebecca Grimes that others would be surprised to learn?

And to what is the one thing that you really want everyone to know about?

[00:47:14] Rebecca Grimes: Okay. So the first one is a really good question. It would be that I went to school for journalism and I spend my first year post college as a police and crime reporter covering murder trials. Like that is what I did. I worked for a newspaper. I covered eight murder trials in 11 months. It was the craziest time of my life. I grew up and had to mature so quickly. Didn't quite know what I got myself into when I took that when I took the job.

But but I then realized, oh my gosh, what did I do? What did I do? And I made it quickly. I pivoted into marketing. And so you know, obviously there were translatable storytelling skills that, that happened here, but I, you know, I'm not a traditional you know, went and got my MBA and did all of this.

I've had a lot of on the job learning. That's helped me get to where I am today. And so But those of you who know me know that this probably also like explains why I have this like lifelong exception with like law and order and TVs shows of like crime, both fictional and real. Because of, because of my history of following following that very early in my life.

So. And then number two the one thing you'd want everybody to know about me. So we talked about that a little bit earlier, but I I am a big believer that it takes a village. And if any, one of your listeners wants to be part of my village, you can find me on LinkedIn. I'm not asking about a ton of other social, but LinkedIn is probably the easiest place to find me.

Connect with me. If you want time with me, if you want advice. I'm here. And if you don't, if you don't reach out to me, find your person maintain maintain those relationships. They matter, I'm working with our CEO Kate Winkler that I met 20 years. When I was a first time director and she was a first time CEO and I saw something in her and she saw something in me and we kept in touch through the years and it's come full circle now in working alongside of her again.

And so invest in the relationships. But I equally do that. So if you, if you don't have your high person I'll be your hype person. I'm here for it.

[00:49:16] Rosalyn Santa Elena: Oh, that's awesome. You're going to get tons of requests. I'm sure it definitely impacts so many people's lives. Thank you. Well, thank you so much, Rebecca, for joining me.

This has been incredibly, incredibly helpful, insightful and just fun. So really enjoy your time and just want to thank you very, very grateful for your time.

[00:49:35] Rebecca Grimes: Oh, back at you. You and I could talk for hours for sure.

This episode was digitally transcribed.

apple podcast icongoogle podcast iconspotify iconrss feed icon

Ready to grow and scale your revenue?

By clicking “Accept All Cookies”, you agree to the storing of cookies on your device to enhance site navigation, analyze site usage, and assist in our marketing efforts. View our Privacy Policy for more information.