Podcast | 11 minute read

Podcast Pit Stop: Pablo Dominguez on Scaling Your Sales Organization

Pablo Dominguez on Episode 13 of the RevPartners podcast
Posted by Kimberly Holcomb on August 2, 2021
Kimberly Holcomb
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Are you planning to double your Sales Team?

"Crew Chief" Pablo Dominguez, expert in SalesOps, shares how to smoothly scale your sales organization on Episode 13 of Pit Stops to Podium. Pablo is the Operating Partner for Sales and Customer Success at Insight Partners, one of the top Venture Capital Firms in the country that primarily invests in growth companies as they begin to scale. Prior to Insight, Pablo was the head of Global Sales Operations at ADP and then at AppNexus. These experiences combined lend to an expertise perfect for offering insight to business leaders and companies looking to grow and scale their sales teams. 

Take 13 minutes to listen and then head back to the races! 🏁🏆

Pit Stop Highlights

Roles & Responsibilities 

The question isn’t “how do I just add 10 people?” But, “what are those 10 roles that need to be added?” Knowing what roles to hire based on your go-to-market motion and what you need is extremely critical.

Ask yourself questions such as:

  1. What kinds of roles do I need to hire?
  2. Is it time to break out a new business sales from our expansion? 
  3. Do I need someone focused on renewals?

Hiring & Onboarding  

“Onboarding quickly and ramping reps is critical, because every month that a rep isn’t onboarding or ramping effectively is money that is lost."

The biggest mistake companies make = false assumptions on ramping. Be realistic on the ramp time!

Ask yourself questions such as:

  1. Do I know the right profile of reps I need to hire?
  2. What is the plan to onboard them and train them so they can be effective?
  3. How do I ensure that they know how to pitch the value prop?
  4. Have I built our curriculum at that point?

Motivation & Incentive

Knowing how to incentivize reps and reward right behaviors appropriately is critical when scaling.

Here are some top tips covered in the episode to designing sales compensation plans and assigning quotas that reward top performance:

  1. Ensure that you reward right behaviors and over-performance - every dollar above 100% is gravy. 
  2. Create a model where everyone wins - if the company wins, you should win!
  3. Establish appropriately ramped quotas that are equitable, achievable, and that foster growth.

Engaging with Pablo:

  • Linkedin: https://www.linkedin.com/in/pabtexas/
  • Twitter @pabtexas
  • Website: https://www.insightpartners.com/

Full Transcript

BT: Hey everybody! Welcome to Pit Stops to Podium, the RevPartners podcast where we talked to execs who competed and won, taking their companies from high growth to high scale. My name is Brendan Tolleson. I am the co-founder and CEO of RevPartners and I am thrilled to have with me today Pablo Dominguez. Welcome, Pablo. 

PD: Hey, Brendon, how're you doing? 

BT: I'm doing well. I will give Pablo's background because that's not usually fair for the guests to actually say what he has done. But for a quick cv, Pablo currently serves as the operating partner of sales and customer success at Insight Partners and prior to Insight served multiple functions. But most notable for this conversation was he was a global head of sales operations at ADP. So what the important thing is, is that Paolo brings both industry expertise, but also on the VC side. So thank you, Pablo. 

PD: Thanks for having me. And really excited to talk to you. 

BT: So, Pablo, I'll give you before we kind of get into the big idea and all, I'd love for you to kind of give a little bit education on who you guys are. 

PD: Yeah, absolutely. So Insight Partners is a Venture Capital, private equity firm based here in Manhattan, New York with 25 years of software, B2B investing. And we invest in growth companies, companies that are scaling, that are coming out of that startup stage and starting to scale. And yeah, we are a huge presence in New York, on the East coast, West coast, a lot of investments in Israel, Europe as well. So, excited to share a little bit about what we do. 

BT: Well, before we get into the big idea, a tradition here we have at the podcast is to get to know our guests outside of the workforce. What are three fun facts that our audience should know about you? 

PD: All right. Fun fact. One is I went to the University of Texas and like most people, you know, from Texas, for the listeners, they love Texas. So I am a diehard everything Longhorn fan, whether it's Women's tennis, just one national championship. Last week, men's swimming and diving won a national championship this year. I follow every collegiate event at the University of Texas. 

BT: What's going to make up for the football team for the last four years? 

PD: Right it absolutely does. 

BT: And tell our audience about your dog. I think that's an awesome fact. 

PD: Yeah so my dog's name is Austin Texas Dominguez so nothing gives me more joy than actually getting his bills in the mail. And it actually says Austin, Texas on it, which is awesome. 

BT: So that's amazing. What else? 

PD: Outside of being a diehard Longhorn fan? Yeah, I love to mountain bike. I actually just came back from moab, Utah, went with four of my buddies for intense mountain biking trip. And now that my kids are a little bit older, it's something I've started to take up again and try to mountain bike as much as I can here in New Jersey. And yeah, it keeps me fit and excited. 

BT: That's great, and you also have a cooking hobby, right? 

PD: I do. So wife and two kids. And my second hobby is I am trying to become a semi-professional smoker, not cigars or marijuana, but smoking. So do a lot of smoking during the week and on the weekend. Ribs, brisket, pork, but you name it. And that's fun. It's a blast. We're coming back full circle to Texas. This is good. I just ordered a smoker from Franklin's in Texas, actually, so I'm super psyched about that. 

BT: That's awesome. Let's  transition out of Texas and let's get into to the big idea. And you already kind of started to get this off pitch, what we're going to talk about. But in light of your experience and where insight is focused, I thought it’d be really great for our audience to understand from you where you sit when they're growing their sales team. What are the things they need to think about? And specifically, if you're looking to double your sales team, there are some key considerations that you have a unique perspective on. And so what I'd love to cover within that big idea is really around roles, responsibilities, hiring and onboarding. And ultimately, how do you motivate the team? So let's start with that first top around roles and responsibilities when they're growing sales team. 

PD: Yeah so again, right. So on the operating partner for sales and customer success. Right so my team is primarily focused on helping our company scale. Right and so the main issue that we see when companies are scaling is, you know, I've got 10 sales reps today or five or 15, and now I've got to continue to grow. And I'm doubling. Right and so to your point, in terms of roles and responsibilities, the main question is not just, OK, how do I add 10 people? I have gone from 10 to 20. The question is, you start to scale is, well, what are those 10 people? Right, am I just adding 10 reps that like the 10 reps. I had before, when you're a startup, you're hiring generals, right? Your reps are selling new business. They're doing expansion. They're probably doing some renewals. They're doing everything right. And so when you start to scale into that growth stage, should I hire account managers and account executives? Do I hire CSM, an account manager in. And so knowing what roles to hire based on your go to market motion and what you need is extremely critical. Right, should I focus those headcount more on btr? Because maybe my top of funnel isn't strong enough or I have too many leads to qualify. Right so we try to help with sales capacity, planning to really inform the s.r.o., the CEO on what types of heads to focus on. 

BT: So what I heard you say there, too, is the go to market motion and forms the type of headcount that you need to create. And there's also that kind of based off of who you're targeting that gets into things like UPS and expansion depending on how the go to market motion works. 

PD: Yeah, absolutely right. I mean, one thing I didn't touch on, but, you know, if you have a strong and direct gtm motion or you want to focus more on the channel, the headcount might be more channel focused. Right, to build out the channel. If you're starting to scale there, if you have a highly technical, complex sale, you may need to invest more in sales engineers. Right which are a very critical role, as all of you know, or product specialists. Right, so it just really depends on your motion, enterprise, mid-market, SMB, indirect, et cetera. 

BT: Well, that's a natural transition to the next topic, which gets into hiring and onboarding. So you have an idea of your go to market motion. You have an idea of the type of roles that you need. Now, how do you think about the profile of a candidate you want to bring on board? 

PD: Yeah, so, you know, when you start to scale your headcount significantly, you've got to be a little bit more prescriptive. Do I know who I'm going to hire? Right, do I need to hire for vertical expertise? Does it matter or is the best? You know, we only do B2B software. So is hiring the best software sales rep from Salesforce going to work in a fintech or an edtech? Right so determining that profile is extremely critical. Second on that piece is, what do I do when they're here? Right when you've got 5 reps or 10 rounds, you know, you're all sitting in a room together in different offices and it's pretty cozy. But when you scale, do I have an onboarding plan for that? How am I going to train them? How do I ensure that they know how to pitch the value, prop the message? Have I built our curriculum at that point? The CEO or the founder can't be doing everything right, like the head of sales or maybe somebody in product marketing needs to step in and provide that. So onboarding quickly and ramping reps is critical because, as you know, every month that a rep isn't onboarding or ramping effectively is money that's lost. 

BT: That’s interesting. In a previous podcast, I was talking to the HubSpot enablement team. And they really have two metrics, and one of them is what they call TDR time to ramp. And it's exactly what you're just describing. It's not just productivity, but it's also how quickly can you get these? Reps enabled and trained. So they can actually carry cuota and ultimately drive revenue for the business. 

PD: Yeah, and back to the time 1 and two together, right. The first question around and roles we talked about was sales capacity planning. The biggest mistake we see companies make is they make false assumptions on ramping. Right, it's like Harrington reps there in my model. They're going to all ramp in six months. We're going to hit our plan. No, it's going to take nine months. Right if it's enterprise reps for longer. And so being realistic on the ramp time and not trying to be overly aggressive will save you on what we missed because we are over. We are too zealous on our ramp times. 

BT: Yeah, it's almost like people planning on the outlier as opposed to what's the norm that gets you into trouble. All right. Let's transition to the last topic. So we talk about roles, responsibilities we talked a little bit about then how do you hire and onboard? But then there's the third leg of how do you keep reps motivated? 

PD: Yep so you now know what roles you have, you're on board. And then how do I incentivize? Pretty simple when you've got a couple of reps to just build a very standard Comp plan. Now you've got reps doing expansion, you've got reps doing renewals, you've got more CS, you've got builders. And so knowing how to incentivize reps and reward them appropriately. Right for the behaviors that you want, are you just paying them to grow their existing base? So you're growing them to land new logos, just net new R.N. and ensuring that you reward for over performance? Right, a lot of companies don't want to pay too much for over performance. And the coaching that we try to get is like every dollar above 100% is gravy like you should. You should pay a lot for that because the reps have done what you asked them to do. Right, so definitely you want to motivate with the highest accelerators possible. Definitely believe in balancing spiffs as well. Right throughout the quarter. You want to incent certain things. You don't want to create an overabundance of stuff because then people get distracted from the Comp plan. But you want to make sure that your quotas are equitable. I can achieve them. And then I'm growing. Obviously, quota setting is hard. When you're small and you're trying to scale, you may not know what a quota should be, right. So we always recommend, hey, set the quotas so that people can enter the financial plan. And then if you go above the financial plan significantly, you reserve the right to review payments above whatever, two, 3% Right but don't cap the plans. Right, because that is very demotivating for the reps. 

BT: Yeah, so the big things I just heard, which I really appreciate since I was in sales at one point in my life, is a reward, the right behaviors and creating a model, which everyone wins, meaning if you're incentivized both the company wins, you should win. And then also from a company perspective, don't be shy to create a model that facilitates that. But also be realistic in terms of how you structure your targets, because if you don't set the targets right. And only impacts the rest, it also impacts you, especially if you have insight or any investor behind you. That's looking at those targets. 

PD: Yeah, Yeah. And you've also got to ramp the quotas, right. Talking about a rebranding like a ramped quota is not just the annual quota divided by the number of months. I'm on plan. Right because the first three months. I'm probably not selling much because I'm onboarding. I'm training on learning. I'm spending time with their reps. So that ramped quota needs to be set also appropriately. So that I'm motivated to be successful. And you don't give me something too aggressive that isn't realistic. Right so I can just take some massaging and time as companies scale, it's hard to get it right. And that's OK. That's why we work. So much with our portfolio companies, because it's an art as much as it is in science. And there's the areas or even just sales cycle and the average deal size that will also impact that ramp. Up to your point, there's the onboarding, but we also have to be mindful of what that actually looks like? That kind of gets back to the go-to-market that you were describing earlier? 

BT: Absolutely well, Pablo, this has been really insightful for me, not to use a pun, but it's been great to hear about some of the best practices that you've incorporated, both from your experience and others, but also what you see across the portfolio inside. So if people want to follow you, learn more about your insight. What are some practical steps that they can take? 

PD: Yeah, I mean, if you are, I'm very active on LinkedIn. Try and share content that we share, that we provide from insight. We have a lot of material in blogs and inside partners.com comments open to the world to view both from a commercial perspective, also marketing, product content, et cetera. Follow me on Twitter, LinkedIn and happy to connect with anybody. If you have any questions, feel free to reach out. 

BT: I really do appreciate your time. I know I learned a lot, I'm sure our audience did as well. So wish you all the best and we'll talk soon. 

PD: Well, thanks, appreciate it.  

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