RiSE Accelerator Founder, Mandy Cole on Hiring 400+ sales reps in one year, and the value of continually seeking feedback.


Powered by RedCircle

Episode Outline

[04:39] Mandy’s background

[07:16] Discovering that running a company, it's evident it's an emotional business.

[10:13] Take time to really take a step back and use data as your foundation.

[11:18] While that looks great in a spreadsheet, it doesn't work in real life because until you have a process that's documented and that you can measure, and that is getting consistent results.

[12:04] Think deeply what needs to happen to hit your goal and direction you’re going to, based on what you have so far, make some assumptions on conversion, what type of pipeline you need, how many new opportunities

[14:34] Consider how many demos there, do they need to have a week or how many discovery calls depending on what type of sales cycle they are, how many discovery calls?

[16:35] Where is our product actually fit right now? And how are we going to attack that?

[17:04] Figuring out how to hold people accountable and then the second part was how to implement that correctly with the team

[19:22] The way to break the sales process into the four main categories

[20:19] Why Mandy really loves mentoring people and leading a team in house

Mandy's inspirations

Mark Roberge

Jeremy Liew

Connect with Mandy

Mandy Cole


Elias Rubel (00:02):

Hey there all you cool cats and kittens. And welcome back to another episode of best in SAS, where each week we take you behind the scenes from conversations with some of Silicon Valley's best and brightest operators and investors, crack a beer, get comfortable and join us on our quest to find the patterns and playbooks that accelerate the sprint to 10 million of that good stuff, that repeatable stuff, that stuff we call a RR. All right, today, I'm super excited to have one of the top go-to-market sales leaders out there on the podcast. Uh, Mandy Cole took, um, took living social from, you know, early stage to over a hundred thousand new merchant relationships. She increased net revenue per sales team member by 300% while she was there. She sits on the board of Mixmax. She was the vice president of sales at Zenefits and a ton of other companies. So Mandy, welcome to the show.

Mandy Cole (01:03):

Thank you for having me.

Elias Rubel (01:05):

So I know I'd love to spend some time talking about what you're up to today because you have rise accelerator, this entity that you found it to help earlier stage companies with their go to market on the sales side. And you're also an operating partner at stage two capital. There's like so much. I can't, I can't even fit it into one intro and it's all amazing stuff, but I I'd love to start at the beginning with maybe what were some things that you learned early in your career, um, that have stuck with you and are lessons that you bring to teams that you help out today?

Mandy Cole (01:35):

That's a great question. And, um, I have learned a lot of things the hard way, um, from making mistakes, but I feel like that's how a lot of us learn from failure almost more than success. A couple of things that come that, um, that I think of at the top of my mind are, um, one is just being, being able to learn from other people. I think it's very natural that we feel like, especially if you're a type a person and I learned this both in sales and then in leadership, how to learn it again in leadership that I don't always know all the answers. And, um, it's very easy for us to feel like we should know that and then try and figure everything out on our own. But the reality is you're going to, you can't be an expert in everything. And so the more self aware you are and the things that you do really well, and then you seek out people that do other things and learn from them.

Mandy Cole (02:28):

You're just going to get there faster. You're going to have better results. And you're also just going to make, um, from a team perspective, you're going to have more engagement. The one example of that is at, um, living social. I, when I first got there, then we had a team of 40 people. We were hiring. I mean, we hired 400 people in a year, maybe 600. Yeah. It was really fast growth. I mean, we would bring people in every week and do these super sessions by the men across the country and then interview them and put them in market. So because expanded from when I got there, it was like 10 markets to 140 markets in one year. And so while you're growing this big team and we're also trying to put an infrastructure and process, um, I felt like I had to have the answers and I had at one point 75 leaders.

Mandy Cole (03:16):

And there were a couple of things, the changes that we made more, you know, behind the scenes around compensation and some process things that I didn't get really anybody's input except for a couple of folks on my sales ops team and rolled it out. And, and it wasn't met with great response. Um, and my, you know, a couple of my leaders gave me some great feedback and they said, Hey, you know, we trust you, but there are a couple of things you miss because these things are happening and we're moving so fast. And it made me realize that I can let go of having to know everything. I was worried that maybe people wouldn't have had as much confidence in me. And the reality is that once I got more input and we did set up committees and they were able to join a committee and different subjects and we would get input before we would make changes.

Mandy Cole (04:02):

Once we started doing that, not only did we have better ideas and make better changes, but I actually had a team that had more confidence in me. And that was a great lesson to learn. And I still see that in founders who feel like they're, that when they're talking about, well, who should we, they feel like they have to own a lot of that stuff versus, you know, hiring people on their exec team that can bring that. Um, so that's one area. The second I would say is really, um, learning to use data, to make decisions. It's very easy. You have a sales to me is a science, but it's, you know, a people aspect too. And with that, it's an, it's an emotional business. And when you ask somebody to put 50% of their compensation in their results, there's a lot of ups and downs that come with that.

Mandy Cole (04:50):

And it's very easy when there's some downs to make decisions on your team's emotions versus looking at the data. And I did that a couple of times where I took one or two people's, well, this is why this is happening. And we made some changes only to find out that that's actually happened to be an isolated incident. So really by now making decisions on data that only I've found that were make better decisions and smarter decisions, but also were able to use that and show the team why. And, um, that's something that I've mentored. Several people on that have been on my teams is how to really take a step back and use data as your foundation.

Elias Rubel (05:28):

So, I mean, you're talking about tremendous scale here, right? Four to 600 people in one year. Um, how, how would you, how are you applying this when you're coaching the earlier stage teams, the teams who are, you know, just setting up all of their processes and just getting into certain habits for the first time, like, what is clean slate, how you set this up, set someone up for success with this.

Mandy Cole (05:52):

Yeah. Um, it's not doing that. Um, and I've had, and I've done that in a couple of places at main street hub, as well as, um, you know, Zenefits, we scaled, I built took an SDR team from 25 to 250 people only to find out that the market opportunity we were going after, we actually did not have a fed in. And that was a very expensive way to do that. Um, so my recommendation to folks is, but it's very normal for people to look at a spreadsheet and have one or two salespeople doing something. And think if I had 10 all doing this, then this is where I'd be in revenue. Let's just go do that. But the reality is that while that looks great in a spreadsheet, it doesn't work in real life because until you have a process that's documented and that you can measure, and that is getting consistent results.

Mandy Cole (06:44):

And then you, you add, you start with your two people and then you add two more and make sure that you don't break it. And then you add two more, then you won't have consistency. And that's when your unit economics get out of whack. That's when, um, and then you also have all these people that potentially aren't performing and you're dealing with, um, motivation issues on top of that. So I don't recommend to people that bodies are the solution. What I recommend is first, what we're going to do is actually build a bottoms up sales model, understand what needs to happen to hit your goal. And we're going to, based on what you have so far, make some assumptions on conversion, what type of pipeline you need, how many new opportunities, um, you know, we also look at obviously who we're going to target to do that. Um, but then let's build the infrastructure and process to make that happen. And then let's monitor that. So we go through, you know, a period where if it's working, then let's add a couple more and make sure we're not breaking it because that's one of the biggest mistakes I see people make is they throw bodies at it and then don't understand why 10 people can't perform like their one person was.

Elias Rubel (07:53):

So I'd love to maybe walk around the different elements on the, on the sales side of go to market that comprise, you know, a sales org, whether it's the process sales ops, um, the storytelling, all the different pieces that go into it. Um, and, and talk about what you see as the most common, like you're sitting at your desk, you, you finish a call with a company that's in the revenue sprint from 1 million to 10 million ARR, and you just face Palm. You're like, Oh man, not this again, you know, and it's just like, you see it over and over again. Could we walk around and do a three 60 of a sales organization at that stage working on that sprint and what some of those most common mistakes are, and if you're even comfortable sharing a couple of real examples.

Mandy Cole (08:42):

So one of the first things that I want to look at is like you said, where they are, how many customers they've sold, who those people are. Um, and so what I typically find is a lot of times, those folks sort of anyone that would sign up, um, and they haven't really narrowed down their, their ICP, their ideal customer profile too. They haven't matched that back to actually what they can sell efficiently and effectively. They've just gone out and said, we want to put people on our product, you know, and we're, we're willing to take anyone. Um, so what I typically find is they're not looking at who are we a better fit for number one, but even number two, who are we retaining? And sometimes they're a little too early, but at least we can do some kind of analysis and a leading indicator.

Mandy Cole (09:30):

Are they at least using the product? Um, you know, so that's one thing that I look at in a lot of times, folks don't have that, um, in place. And, you know, so we'll talk about, we have to do some analysis on that. And then the second thing I look at is, you know, when we start talking about whoever's selling and how they're selling, and we start digging into that, um, there's no KPIs that they're measuring on a daily or weekly basis. So it's pretty much, well, this is the quota. And so when I start to dig into, okay, well, how many, how many demos do they need to have a week? Or how many discovery calls, depending on what type of sales cycle they are, you know, how many discovery calls do they have? How many qualified opportunities are they creating a week? And there's, you know, crickets, well, I don't know how many of those move forward.

Mandy Cole (10:25):

How many people do you need to reach out to, or even have a conversation with to get a discovery call booked. So there's no real understanding of the pipeline that's needed and what their conversion rates are looking like, except for maybe just pure like lead. This is how many marketing qualified leads we got into how many deals we did. Um, but when you have that whole gray area in between, you need a plan. And that's the biggest thing. One of the biggest things I see people are missing, they're missing a plan on what my sales person needs to be doing so that I know that they're going to hit this number. And also, so they know what to do to be successful. And then they need a plan on, um, you know, some of the things I know you're familiar with Eli, but it's the targeting piece.

Mandy Cole (11:05):

Who are we going after? Who makes the most sense? Where is our product actually right now? And how are we going to attack that? Isn't an inbound motion. Is it an outbound motion? I, you know, so we just had a client that we worked with Maddie, who is, um, they do identity fraud, um, and there have a great product. Um, and they started in Mexico. That's probably 60% of their customers, but they needed to move up market, but they were relying on inbound to drive them up market. And the reality is the more that you're moving up market, the types of folks that they're meeting with CSOs of these, you know, companies as we size them, they're not producing inbound leads. So we had to build obviously a whole outbound, um, process motion for them. And now they're seeing a lot more attraction there, but it's one of those things where they just assumed we'll just try and target them and they'll come in. And what they were finding is that they're the team they were paying to do mid market, was spending a lot of time trying to sell these small deals. And so their unit economics were out of whack. I mean, their payback period was 24 months. And so by sectioning those two, having an SMB, putting a different person, that's actually just taking those inbound leads and closing them on one call and really then focusing them on mid market. We've been able to, um, you know, cut that, um, you know, economic Simon, half

Elias Rubel (12:26):

That lack of a plan. I'm assuming that sparks the inspiration to start rise accelerator. Can you, can you walk us through, like what you, you know, you had been doing these really high growth, really big stints as a leader in sales, and then you changed course a little bit to I'm assuming deliver your learnings to a, an earlier stage market or what, what brought you there

Mandy Cole (12:49):

Exactly. In all three of my, um, in my last in house. So at, um, let me social main street hub and Zenefits, you know, I was tasked with not only growing this team really quickly, but also, um, increasing productivity and stabilizing productivity so that we had the right unit economics. So trying to do those two things at one time is, um, a big challenge. And I quickly realized unless we had a very standard process and we had backed into here's what they need to do each week to get there. And then we had leaders that actually measure that. And that's the second thing I see people do is they'll, there's a plan and they get, Oh, okay, well, this is what we need to be doing. But then nobody's actually, we're not, they're not managing their team, those numbers, and they're not actually thinking about, and they're not bringing marketing it right.

Mandy Cole (13:37):

And saying, okay, marketing and sale marketing and sales, aren't working together. So they're both doing separate things. And there isn't this, you know, as a team, we need to create this much pipeline this month in order to have, you know, 60 days down the road in order to hit this number. And here's how we're going to do it. And here's what sales is responsible for. And here's what marketing's responsible for. So, you know, having the plan is the first step, but then actually managing to that and looking at those numbers every month and figuring out why, if something's not happening, why that's not happening. So all of those companies and each company, we iterate it more, it was, you know, figuring out what those were, how to hold people accountable for. And then the second part was how to implement that correctly with the team.

Mandy Cole (14:21):

I'm not a big fan of training where you bring everybody in. And so it's still happens all the time, right? Like onboarding trading is what we put people through these three full days of learning about our company and our product and, you know, and then we just set them off into the wild. And, um, so throughout that, um, one of the things that I developed with my sales outs team was, um, because I'm a very big student of how people learn was, um, a more integrated implementation program. And we now do this with our clients where it's four weeks. So once we stand up the process and the tools and set up and training them in two days, we basically break the sales process into the four main categories, prospecting discovery, demonstrating value, and closing objection handling. And then we focus on one of those skills a week and we do that in a variety of ways.

Mandy Cole (15:12):

So we use video, you know, we record an elevator pitch, they give feedback on each other. They have to write it out. They have to shadow two people. They have to join to like interactive games. So there's a lot of ways that they practice just that one skill and I'm able to see it because we use an LMS so I can give feedback as well. And, um, and then they talk about their successes at the end of the week. And then we recap as a team and it's gamified. So they earn points for doing these things. But one of the things that we've found is that these lessons really stick because they actually have to practice it. And then they have to, and not only that, but then they start sharing with each other. So, um, I mean, I'll revert back to Maddie cause they just graduated from this program, but the sales team there, which was six or seven people, not huge, but that they are performing so much better now from going through this program.

Mandy Cole (16:04):

And their feedback was, this is one of the best we've gotten to learn from each other. We know each other better, but we also learn some really good standard sales methodology that we've never learned at other startups. And so being able to put that kind of program in place that I saw work in house when we were having to scale people up so quickly. Um, it's interesting because I feel like there's this thing about startups where structure feels bad sometimes, but the reality is is that people operate well in structure. They want, you know, salespeople, don't like gray, they like black and white. And so the more that you can give them a plan and a process and teach them how to do it, actually, the more successful they are.

Elias Rubel (16:48):

It makes perfect sense. So now I want to talk about you a bit like personally. So, you know, to most of our listeners, you are at the very pinnacle of career. And I, you know, you're, you're only continuing to gain steam. I'm curious when you think about, you know, last year and the year before, and then reflect on what your own personal goals are for this year, you know, like what, what is the next step for you and your career and what challenges are you trying to, um, work through through yourself?

Mandy Cole (17:17):

Great question. I think, um, last year to this year was a big step for me. I, you know, for the first year and a half that I had my own firm, even though I loved it. And I love working with companies at this stage, they're still a little bit, I still was recruited all the time. You probably are too to come back in house. And they're still a little bit like it's, it's probably one of the most challenging things I've done to go out on my own and not be, you know, I really love mentoring people. I loved leading a team in house, but one of the things I found is because of my experience, those are the types of rules I got roles I got recruited for versus early stage. Um, and an early stage probably in house isn't maybe the best right fit for me, which is where, you know, the rise accelerator idea came from, um, with the encouragement of some VCs that wanted help for their portfolios.

Mandy Cole (18:14):

But so I think, you know, for me to take that leap and go out on my own was a big step. And then the second leap was hiring people on my team. So I did not, um, last fourth quarter of last year because we were growing, we had more demand than I could handle. And also I needed, you know, going back to that, don't be the roadblock and get expertise. I needed people that were better at sales ops and structure than I was. Um, and that can really, I mean, we're building out whole technology stacks for people we're mapping out our processes where, um, you know, putting lead routing systems in place. So in order to do that, I needed a couple of folks that, um, had that. And then the other thing that my clients were asking is you're building this plan and, you know, the people we're hiring can't, you just hire them for us.

Mandy Cole (18:57):

And so, you know, that's another big step of bringing people onto your team that you are now paying for. So I think, you know, going from last year this year, my goal was okay, we've got now, like, let's see, you know, let's continue to scale this and also look at how our program is evolving. And that's where the phase two program of continuing to manage rev ops, um, for our clients came from. Um, so our goal this year is to double revenue. Um, we are on track to do that, um, with a little bit of a clip from COVID, um, mostly things that just pushed back a little bit because they were getting funded and waiting on their funded funding. Um, and I think that my other goal was just to continue, you know, it's, for me, it's always continuing to look at what kind of value are we providing for these clients.

Mandy Cole (19:42):

And can they say, because, you know, when you're in this kind of business, even though we're much more than a consultant, cause we're actually, I mean, that's why we call ourselves an Excel. Like we actually sit with their team and do the work, but it's, you need people to say like, yeah, I couldn't be where I was without them. And you know, so I'm constantly evaluating and getting feedback on where we could continue, how we can get to that. So for me, getting to that number just means that we're proving value and that's the most important thing for me. The other piece was, um, you know, really getting more on experience on the investing side. And that's, what's been great about spending time and joining stage two is that I'm able to use my skills on the go to market side to help, um, the stage two portfolio companies have those same results in a little bit of a different way, but then I'm also learning more about, um, you know, using my skills of evaluating companies to look at new companies. And that's exciting.

Elias Rubel (20:42):

How do you unwind when? I mean, your work, your work life is incredibly intense and you know, you've have a ton of drive. How do you, how do you unplug from that?

Mandy Cole (20:51):

That's a great question. I'm sure everyone struggles with that. I don't, I've had to teach myself over the years, um, to be more scheduled and honestly I have three kids and I think they helped me do that because I mean, not so much the last two months, because we've all been are a couple of months ago, I've been sort of sequestered in our homes, but before then they have activities. They have, you know, the nanny leaves at a certain time. Um, and they're in sports. So the reality is that I had to be able to, um, be a lot more disciplined around how I use my time and prioritizing. Um, I do every Friday, um, before I quit, I look at next week, I make sure everything's scheduled. I well, and I say quit, but still do some stuff on the weekend, but before I like actively, you know, make sure everything's scheduled.

Mandy Cole (21:42):

I, um, so for me, a lot of it is like aligning here are the things I need to do, but do I have actually have time on my calendar to do all those things? Um, and that's a time management technique I picked up a few years ago. That's really helped me. I mean, when I was in house, for those of you that are still, I used to block off four to five on my calendar every day and just to have time to catch up at the end of the day, but also my team knew those were open hours. So if they needed something that day and I hadn't gotten to them, they could typically ping me then. So just finding times, I think the biggest thing is just blocking calendaring yourself really. Um, outside of that, I mean, we do a lot of hiking. We do a lot of, um, now biking, my kids are all old enough to bike, which is fine. Um, we were doing a lot of traveling, not so much anymore. Um, and you know, so just really enjoying where we live in Marin.

Elias Rubel (22:32):

Nice. Awesome. And then last question, as we wrap this up, um, who have been some influential folks in your career who either as mentors or peers, who you look up to just, just folks out there doing great work that have helped you get to where you are today.

Mandy Cole (22:48):

Yeah. Um, so you mentioned Mark. He, um, Mark Roberto has been influential to me. We met when we were both, um, he was growing HubSpot and I was growing, living social and we were introduced, um, by a mutual friend and, you know, we both realized quickly that we had similar challenges, similar methodology. And so he's been somebody that I've been fortunate to have to bounce things off of. Um, one of my early mentors, um, that's helped me throughout my career is Jeremy Lou. He's a partner at lights speed. And he, he actually gave me the best feedback originally when I was at city search and I was going from my first leadership position. And, um, another colleague of mine got the, um, role over me and I had been there longer and I thought I was doing a good job. And so I was mad, you know, and I, and um, but I went to him and I said, I want to understand why I didn't get this role.

Mandy Cole (23:44):

And he's been so great about giving me feedback throughout my career. And this is the first time he did. And he said, well, because I want you to continue to practice. Like sometimes you, when there are questions come up, like in front of a team, you're very passionate, which is great, but you don't know how to control that. And you will just say, no, I think we should be doing this. And as a leader, you have to understand how to manage that in front of a team. And he was right. Um, you know, and so he's been, um, instrumental. He actually, um, my new place, which is a company that I right before living social, I took them from zero to 20 million. He recruited me there and then he was on the board of living social and recruited me there. So I've been fortunate, but along the way, he's given me some pretty tough feedback.

Mandy Cole (24:30):

That's only helped me. Um, so I encourage people to seek out other folks that you work with or other mentors, because, um, and then I've got a few other folks in the, um, BP and even people that worked for me that, um, I still regularly talk to and bounce things off of, cause they're at different companies now. So I just encourage people to find those types of folks because we get so, you know, everybody, we all just get so heads down and what we're doing and having those conversations just, it's so important for you to just be able to think about maybe something you're doing differently

Elias Rubel (25:10):

Completely well, Mandy, this has been a really fun conversation for me. I'm sure our audience is going to get a, you know, a ton of actionable tidbits out of this and some great strategies to, um, to test out on their own. So thanks so much for taking the time and recording with me today.

Mandy Cole (25:24):

Thank you. I really appreciate it.