Podcast

If You’re Not Failing, You’re Not Learning – Rebecca Grimes

Empathy and compassion are the leadership building blocks Rebecca Grimes has built her foundation on to allow her team to be vulnerable and accept failure as a means to grow and learn.

In this week’s episode Rebecca Grimes, Chief Revenue Officer for Ruby.com breaks down how she accomplished exponential growth as a fairly new leader during such a tumultuous year. Her skills in B2B and B2C marketing has led large scale growth for a number of SaaS companies.

She has been named an Ignite Visibility’s Courageous Marketing Leaders in 2020, 2018 Women to Watch in the DMN Marketing Hall of Femme and one of the top 25 Mobile Women to Watch in 2014 by Mobile Marketer.

Tune in to learn how Rebecca pushed through the uncertainty of leading a company during such a tumultuous year!

Watch or listen to this episode:

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Transcript:

Thu, 7/29 1:28PM • 29:09 

SUMMARY KEYWORDS 
ruby, data, sales, business, marketing, crm, people, lead, pandemic, team, segments, understand, met, service, career, leader, small business, processes, sales team, years 

SPEAKERS 
Intro/Outro, Rebecca Grimes, Christopher Smith 

Intro 
Welcome to the Sales Lead Dog Podcast hosted by CRM technology and sales process expert Christopher Smith, talking with sales leaders that have separated themselves from the rest of the pack. Listen to find out how the best of the best achieve success with their team and CRM technology. And remember, unless you are the lead dog, the view never changes. 

Christopher Smith   
Welcome to Sales Lead Dog. Today we have joining us Rebecca Grimes. Rebecca, welcome to Sales Lead Dog.  

Rebecca Grimes   
Thank you, I am excited to be here today.  

Christopher Smith   
I’m excited to have you on the show. Rebecca, tell us a bit about your current role and your company. 

Rebecca Grimes   
Sure! I am the Chief Revenue Officer at Ruby.com, and my responsibilities include sales, marketing, partnerships, and customer success. So the entire journey from becomes a lead to Ruby all the way through ongoing retention and growth. And Ruby is an incredibly special company. We are a Virtual Receptionist and chat services company that focus specifically on the small and medium sized business community. And so deep roots, almost 18 years old, but really deep roots in community building and giving back and the the responsibility that we feel for in service to the small business community and how those moments matter and the care of the customers that we take with our with our employee base and making sure that there is, you know, every call gets answered, every customer feels heard, no lead gets missed, whether that comes through the website or through the phone is really in the fabric and DNA of all Rubies. 

Christopher Smith   
And Ruby, I’ve been hearing about Ruby forever. You know, as an entrepreneur, I think you’d have to pretty much live in a hole to not know about Ruby. It really is a great company, and I’m thrilled to have you on the show.  

Rebecca Grimes   
Thank you.  

Christopher Smith   
When you think back over your career, can you tell me about the three things that you believe that really contributed to your success? 

Rebecca Grimes   
Yeah, you know, I think it starts with the fantastic people, coaches and mentors that I’ve had the opportunity to meet either through my network or through the roles that I’ve had across several companies. Today I am at Ruby because I met Kate Winkler, who I know as Kate Edwards, because I met her before she married her, her husband. But we met very early in my career, she was a first time CEO, I was a first time Director of Marketing and, and I would go on to work with her in another company, and and then we would just stay in touch through the years. And so, you know, when she joined Ruby, I was incredibly excited to hear that she was joining this special company, and and then, you know, a handful of months later an opportunity presented itself and she’s one of those people that that you follow. And I’ve been very blessed to have several folks like that, that I’ve met in my career. I would think, you know, that’s very related to just the network. And you know, by design, Chicago tech is a small world, and and that has changed over the last 10 years where it is no longer Chicago tech, it is a small world as tech is a small world. And, and I you know by design, you know carve out time to network and spend time meeting new people, learning from others, networking, and it is probably the last thing that’s always on the to do list, but it is one of the most important things that I have found have contributed to me bringing on talent, to me getting new ideas, to me meeting new people. And so, you know, that’s an important contributing factor. And then I think the last thing is you know, I I’m a get-shit-done kind of a person, I had to become comfortable living in a state of change. And I know that that isn’t easy for many people. But you know, usually when I’m brought into an organization it is to, to scale, to rebuild, to start from scratch. And, and that requires being comfortable that what we did yesterday is now what we’re going to do today, and it’s sure not what we’re going to do tomorrow. And I think that, that most of the companies went through years and years of changed management all in a handful of months when the pandemic obviously hit last year. But I you know, I saw that as an opportunity to really push Ruby into a new place alongside the rest of the leadership team here. And, and so I, those are probably the three things that come to mind. 

Christopher Smith   
That’s tremendous. Now, you’ve started your career in, or your sales career as a marketer. Can you tell us about your journey? 

Rebecca Grimes   
I did. I first started out, I went to school for journalism. I did that for 10 months. I had all the regrets moments into my, my first few weeks as a as a reporter, but I had undergrad in marketing and comms that obviously helped me pivot and transition. And I started out as a one, one person out of a 12 person proposal center, App Service Master. And so I was in marketing, I was packaging up things to help accelerate the sale. And for those of you who remember, RFPs used to be these super thick binders that you had to FedEx in overnight, make copies of and, and that’s what I lived in and so I got a flavor of marketing and sales very early on in my career. I would then spend, you know, the next 10, 12 years you know cutting my teeth against all disciplines of marketing, but when I, when I found myself at Vibes, I spent the first few years completing a pivot into the enterprise retail space with mobile marketing. And I wanted to learn sales, I worked alongside sales for all of my career. And so we just brought on a new head of sales, I, I said, “I’d love to build out this team with you.” We were going to be rebuilding this team from scratch processes, building out a BDR team solutions consulting, what is our enterprise go to market model. And all of that, you know, really made me a better marketer, it helped me understand what lead quality looked like, how all leads are not created equal, what the real kind of partnership needed to look like between sales and marketing organizations. And so I would, you know, then go on to, you know, run marketing again. And then at Ruby, I, I run both sales and marketing, so the and the partnerships team, so the full, the full growth and and now the retention team with, with my recent promotion to Chief Revenue Officer, 

Christopher Smith   
Was that a difficult transition or, or to step into this current role as a CRO coming from a marketing background, now you’re leading the sales organization as well?  

Rebecca Grimes   
You know, the two years that I spent in sales leadership at vibes, you know, that that was an enterprise, you know, opportunity and the the heartbreak of, you know, working so hard on an enterprise deal only to not be awarded that business or the success that you would celebrate after working so hard. And, and winning, winning that logo, you know, it definitely is a very humbling role. Sales is a grind and, you know, people by design, choose that as a career or think that they want a career in that and move out of it. And, and what what I really appreciate in the current role that I have is that the the sales process is is unique, we’re, you know, we’re selling to small businesses, and, you know, the enterprise sale the cycle, the length, the duration is incredibly different than what we do here. It is about trust building, relationship establishment, these are mostly conversations that happen over the phone, not in in-person or face-to-face via Zoom. And these small business owners are, you know, potentially running between jobs and in their car. And so we have, moments matter when we’re, you know, when there’s some arc of pain, that’s, that’s got their interest of wanting to learn more about our services. And, and so we have, we have, you know, a unique opportunity to help them understand our value and, and that sales process has evolved to be this incredibly consultative selling process over the last 14 months since since I joined Ruby and as we brought in new talent, because the the needs of our buyers are changing, and especially over the last year, those needs have have changed. And so I think that I I am both a better salesperson and a better marketer, because I straddle both worlds all the time. 

Christopher Smith   
Yeah. The, when it comes to to sales leadership, I’ve talked to many people on the show, and they’ve talked about the importance of having a great team. When you came into your current role, what do you do the first 90 days? 

Rebecca Grimes   
I did a lot. My first 90 days, the pandemic was introduced in the first 90 days after I joined Ruby. So, you know, I start by listening. I think that that is critically important when any new leader joins an organization there is a wealth of knowledge in terms of what’s working, what’s not working, things that we need to be priorit, prioritizing. And so I met you know, my first few weeks there was meeting every single member of the team and listening. And, and and from there, then really building out you know, what, what is that path forward and we built out a plan and I built out an org and then the pandemic hit, and that changed everything. And, again, that constant state of change, it was okay, let’s regroup. What’s our path forward? You know, first week we had to get all of our, you know, 550 team members remote, you know. These are people that have desktops and multiple monitors and equipment and, you know, not dedicated office space in their homes. And so we had, we had a lot of work to do there and, you know, in particular with our, with our sales team, very similar setups that we had to, you know, replicate and create, you know, without losing a business, that we’re a 24/7 business, so we have to keep going as we’re, as we’re shifting and evolving. And I think that, you know, the the first, you know, priorities that I wanted to understand, after we got through all of that were what are the KPIs that we measure ourself on? What is the data that we have access to today? What is the data telling us that we should be doing potentially differently, and then obviously, when the pandemic, you know, hit small businesses with shelter in place, you know, we had to regroup as a business, what did you know, we have, you know, customers that you can, you know, cancel with 30 days notice, and, you know, businesses that shut their shut their doors didn’t need us for that service. And so, you know, we had a responsibility to the rest of the Ruby employees to figure out how to market and sell in a very complicated landscape with the small business community, and we started by listening. What are the what are the resources that the small business community needs to figure out? They need to figure out how to lift and move to remote business, they need to figure out how to apply for the PPP loans, they need to understand if this is going to be short term or long term, and if it’s going to be a long term, how do they stand up a business without a physical location anymore? And so a lot of it turned into, you know, educational content that we were producing from a marketing perspective. And then from a sales perspective, who were the least impacted small businesses that actually really needed us right now, and then where was the data telling us we needed to be? And so there was a lot of, there was a lot of things that were all happening in parallel at the same time, and probably one of the biggest moments that I had very early into my time at Ruby was we were, we were a sign up based sales model and marketing model. And so we counted how many new customers we acquired. And what that did not tell us was, how much money were those customers spending with us on a monthly basis? Where were the growth segments coming from? How did we need to potentially market and do segmentation to either bring more of one segment in or another? And so you know, flipping that model, upside down, redoing comp plans, redoing dashboards and KPI measurements, partnering with finance to understand how to translate a sign up target into an MRR target, and then, you know, how did that impact our MCAC and LTV to CAC? And so everything from a KPI perspective was flipped upside down in the first 90 days by design to make sure that we understood what we were building and growing and being accountable for. 

Christopher Smith   
Listening to you, it sounds like your marketing background really came in handy in this crisis time. 

Rebecca Grimes   
It did. And you know, again, I was surrounded by a fantastic team who were helping me with the knowledge gap that I had about Ruby and our processes and our systems and our tools. But, you know, arguably, you know the SMB community is so unique and, and I, my first job was working for a small business. And so I have always felt deeply connected to small businesses. And so it was this rallying that we needed to do and it started with us at the at the point of how do we engage with this community? And that is marketing, that’s marketing’s job. And then sales’ job was to how to understand if there’s value in our services and sell that. And, and then from a partnerships perspective, who are the partners? You know, we started, we have a big legal services base, we started partnering with our bar associations to provide content to help navigate, you know, lawyers have physical offices, how do you, how do you bridge that gap and continue to service your customers in a remote way? And so we were just very focused on the needs of the community, and the growth came after we focused on the needs of the community first, 

Christopher Smith   
Do you think the fact that you were coming in from the outside when all this happened, and you’re so you really didn’t have that that knowledge in your head about how the company worked, that you’re able to come in with a truly fresh perspective, do you think that helped? Or do you think it was harder? 

Rebecca Grimes   
I think I think in some times it helped and, and sometimes it was harder. You know, one of the one of the fantastic things about about Ruby is that we have such deep tenured people inside our organization, one of my sales team members has 11 years at Ruby out of the 18 years of the company’s history. And, and so, you know, that from that perspective, you know, meet me coming in with a fresh set of eyes was, you know, there was a lot of change that happened. You know, there were new tools that we had to implement, I mentioned the KPIs that we flipped upside down, we evaluated our processes, our go to market strategy, everything was up for consideration. But I also think we would have done that, irrespective because of the pandemic, and it would have forced us to, to have those conversations, but I was less emotional about those change management decisions because I, I didn’t build, I didn’t build any of that, that that that process or that systems or that go to market strategy, and it allowed us to really let the market lead us where we needed to go, you know, without without bias of you knw emotion around like we did this, we have to, you know, we’re all in on this versus what is the data telling us that we need to do. I’m a very pragmatic person, and I live in data dashboards, and with a curiosity to dig into things that look off. And, and so again, you know, that, that I think that that lended itself to us, recovering in the way that we did and, and, you know, getting to a place of you know, hiring a bunch of new talent last year, in a in a time when you know, many, many folks were laying employees off. 

Christopher Smith   
Right, right. Looking back over that time, is there anything you would have done differently? 

Rebecca Grimes   
I’m sure there’s lots of things that I would have done differently. You know, probably one of the most, you know, one of the most notable things was that we hired a bunch of people that never got a chance to meet each other. And, and, you know, we started implementing these daily stand ups that were done, you know, remotely. And before that, we would do a little dance party where we’d play some music and catch up and it was, you know, social interaction. It you know, for, for me, I think that if we had known how long we were actually going to be apart and that these weren’t people that were going, I hired a VP of Sales that has not met his team ever. And we’ve hired 20 plus people on the sales and marketing organization over the last 12 months, again, that have never set foot in office. And I think that, you know, we we had to navigate how to extend culture and connection back to Ruby in a way where if you walk into our offices, you’re immersed in who Ruby was as a culture, and I think it took us a little bit longer as an organization and then with within my team to figure out how to do that in a remote world. And we’re still figuring that out, too. 

Christopher Smith   
As a leader, how is it, how important is it for you to show vulnerability to your team? Is it important? 

Rebecca Grimes   
I have done presentations on leading with vulnerability it is it is one of those those leadership qualities that I observed in Kate, our CEO, very early on in my career. And I’d like to think that I’ve taken my leadership, like little pieces of all of the fantastic leaders that I’ve had over the years, but that was one of the authenticity, Authenticity, vulnerability, those are some of the qualities that I’m drawn to naturally as a human being. And I don’t know how to be any different as a leader. And so I shared on LinkedIn yesterday that I was on a meeting with my team when the verdict came in, I visibly cried in front of my team. I think that it is the acceptability of being vulnerable in front, especially now like with everything that has happened over the last, you know, 14 months since the pandemic started, leading with compassion and empathy and, and letting people have space and take a moment is, is something that is probably going to be expected as, as you know, businesses continue to evolve. And I, I remember early in my career, you know, being surrounded by, by leaders that that were not vulnerable, that, you know, were very business is the only thing we’re ever going to talk about, but didn’t make an investment to know me as a human being and the things that I was passionate about and that I cared about and didn’t take an interest in what I wanted to do next and how I wanted to be challenged and what growth looked like for me and, you know, I, I was I was drawn away from leaders like that. And so again, I think that, you know, my leadership style has been formed by both the best of who I’ve had the opportunity to work with and some of the folks that, you know, candidly, I probably wouldn’t work with, again, because we just fundamentally differed on on the leadership style perspective. 

Christopher Smith   
Do you share mistakes you’ve made in the past with your team? 

Rebecca Grimes   
Yes. I if we are not failing, we are not growing. And it is it is something that we are constantly pushing on each other. I think that, I think that there are some people that either, you know, prior to joining Ruby, have had an experience where there’s been punitive damages for failure, and I think that that, that has created a bit of PTSD for employees where, you know, if I make a mistake, I either have to cover it up or I’ve got to deflect blame somewhere else. I’m a big believer that you own it, you take accountability. Even if it wasn’t you, you fall on the sword, and you learn from it, and you create a path forward. And I think that that we are, we we have on our Fridays, during our stand up, our Friday theme, we have a theme for every day of the week, Friday is Friday fails. And we talk about them every week as a team and we share you know, we share funny stories of failure and we share actual, you know, really things that that impact each other that again, vulnerability, we have to create a safe space where there aren’t consequences for sharing things like that. And we’ve worked very hard to to create an environment where that is acceptable and expected that you are failing all the time. 

Christopher Smith   
I love that. I love that. Because that, to me, that’s I mean, you said earlier, if you’re not failing, you’re not learning, you’re not moving forward, you’re not growing, couldn’t agree more. Let’s shift to one of my favorite topics: CRM. Do you love it, or do you hate it? 

Rebecca Grimes   
I, there’s a love hate relationship that I have with a CRM. Obviously, it is a necessary evil, it is how I how I forecast how I understand the health of the work that we’re doing both on the growth and on the retention side, the segmentation of you know, what is happening within our customer base and our prospect database, it is it is this necessary evil, I will say that it gets you know, more and more complex and, and, you know, the the the ability to really scale a business without having to overhaul processes is becoming more and more difficult to to navigate. And so we know we’re going through a new funnel, revamp, and modeling right now exercise, and it’s one of those painful cans that has been kicked down the road. And we couldn’t tackle it last year with everything that was going on, and we ripped and replaced a bunch of the underlying tech that we have. And so this was that last piece and it was okay, we’re gonna do it. And most of the meetings are, oh, there’s a lot of work to do. And and again, I think it’s a constant state of changing as we want to better understand and capture more data so that we can service our customers better, it means that that we need to constantly be challenging what that CRM delivers for us. 

Christopher Smith   
Right. I think it’s a leading question for you a little bit based on what you said, but one of the things that I see when we go in and look at CRM for companies where they’re telling us, “Look, it’s just not working for us,” is they’re not spending enough time or they haven’t spent enough time aligning their data to really support their strategic goals. Can you talk about how you’re doing that at Ruby? 

Rebecca Grimes   
Sure, a great example of that would be our, you know, our vertical or as we refer to them as our segments. And so we’ve got key segments that, you know, historically, we have found success in. And then there are new segments that emerged last year as results of the pandemic and new segments that needed our services. And there, there are some very broad categories that we had defined like Home Services as of for instance, that could mean everything from an umbrella contracting business with multiple different skills that sit beneath that, or it could be a local plumber, or a roofing company. And so Home Services is a broad category. It’s incredibly hard to understand what are the needs of that unique business if you don’t understand the sub segments, so that’s a great example of how do you go historically identify sub-segments of legacy data and existing customers that aren’t easily identifiable? Sometimes the plumber doesn’t have a website, you know, they, you can’t tell from their name what they potentially might do. And so, you know, that’s, that’s just an example of, you know, as we grow and evolve, it isn’t just about making a change in the system, it’s how do you have pattern-recognition data that’s historical that you either map to the new process that you want to have in place, or you have data gaps that you have to fill in, or you just accept, I’m not going to have that data. And if you’re like me, I want all the data, I want it to be mapped. I want it to be accurate. You know, wow, what we did a year ago isn’t gonna be what we’re probably going to do tomorrow. It’s definitely informing either what we do or don’t do on what we spend more time focused on or what we tried and failed and don’t want to repeat that same mistake. And so again, you know, I think that that you know, that that but you can over you can over index as well. I think we’re experiencing that, like you can try to have so many data fields that the sales process takes an extra 30 minutes in our case, you know, we’re very transactional in nature. So we’re closing, you know, 20, you’re signing up, you know, 20 to 30 small businesses a day. And so, you know, every 30 minutes that you add to that, that’s almost a full time headcount. And so how do you balance the needs of the business to have data with also the consumption of the salesperson and the marketing teams time from a campaign perspective, in order to find that right balance? 

Christopher Smith   
What’s your, you know, thinking back over your career with CRM, what has been the biggest pain point or struggle when it comes to CRM? 

Rebecca Grimes   
I think that, um, I think that two things. I think data integrity and adoption I think kind of go hand in hand. And so, you know, similar to what I just was, you know, talking about with the sales team, if you make everything a required field, and then they don’t know the answer, they will make something up to fill in that field. And so you’ll immediately lose data integrity right at the at the, the onset of that. I think the the other kind of side of that coin is that if it doesn’t actually map to the funnel that you’re taking people through, from a forecasting perspective, it is really hard for you as a revenue leader to understand where your growth is going to come from, what your probability of hitting plan is, and then how fast there are levers that you can pull to either accelerate the growth of the business or pivot into a new segment or ICP. And so all of that, you know, depends on, on confidence level in the CRM, and the data integrity that sits behind it. And no matter how clean you think your data is, it is never as clean as anybody like me is going to want it to be and how most of my team want it to be, and finding that right balance there, sometimes done is better than perfect and directional data is better than no data. And and, and really like what are the really required fields that we need to have? Because usually that starts at the front end, so if you put your marketing hat on, how many lead capture form fields do I need to have in order to effectively remarket to this? And there’s new technology like progressive form filling where you recognize where the cookies, somebody has been to your site, and I ask for two more pieces of data before they interact. And so things have changed, and they’ve constantly evolved. And after we asked for two, we’re like, oh, but we really want these other two pieces of data, too. It’s this constant evolution. We never have enough data, but you can’t hop all the data. 

Christopher Smith   
No, no, it is, you said it. It’s a balance, and finding that balance, the problem is how it’s never, it’s always shifting, it’s always moving. You know, it’s never static, which keeps it interesting. We’re coming up on our, our time here. I think we actually went long, because I just love listening to you. If people want to find out about Ruby, what’s the best way? 

Rebecca Grimes   
You can visit our website at Ruby.com. There are, there are bundles of packages that we offer, and we also have this incredible partner ecosystem where we have integrations and partnerships with many other companies that again align and service to the small business community. So that’s the best way. You can also find me on LinkedIn, and I’d be happy to point you in the right direction of folks here, here at Ruby. 

Christopher Smith   
Yeah, that was my next question. So you read my mind. So Rebecca, thank you so much for coming on Sales Lead Dog. It has been absolutely terrific listening to you. 

Rebecca Grimes   
Thank you. It’s been a pleasure. Thank you so much.  

Outro 
As we end this discussion on Sales Lead Dog, be sure to subscribe to catch all our episodes on social media. Follow us on LinkedIn, Facebook, and Instagram. Watch the videos on YouTube, and you can also find our episodes on our website at Empellorcrm.com/salesleaddog. Sales Lead Dog is supported by Empellor CRM, delivering objectively better CRM for business guaranteed. 

Quotes

  • “I’m a big believer that you own it, you take accountability, even if it wasn’t you, you fall on the sword, and you learn from it, and you create a path forward.” (24:16-24:25)
  • “When any new leader joins an organization, there is a wealth of knowledge in terms of what’s working, what’s not working, things that we need to be prioritizing.” (13:27-13:35)
  • “I think that is the acceptability of being vulnerable in front, especially now, like with everything that has happened over the last, you know, 14 months since the pandemic started leading with compassion and empathy and, and letting people have space and take a moment is, is something that is probably going to be expected.” (22:22-22:45)
  • “And we’ve worked very hard to create an environment where that is acceptable and expected that you are failing all the time.” (24:53-25:00)

Links

Rebecca Grimes: LinkedIn
Ruby: LinkedIn
Ruby: Website

Empellor CRM Website
[email protected]
Empellor CRM LinkedIn