Share this article

Learn from the brightest minds how to predictably and efficiently grow revenue.

Related Content

You Can’t Sell to Someone Who Can’t Buy with Michael Dalley, CRO at Aerial Vantage

In this episode, Guy and Michael explore the lessons Michael has learned over his twenty years of sales leadership experience. Discover the importance of forecasting accuracy, the potential of the Challenger methodology, and why you can’t sell to someone who can’t buy.

From Inbound to Outbound: The Sago Sales Transformation with CRO Katharine Reagan

Katharine Reagan, CRO of Sago, joins the Revenue Insights Podcast to share how Sago pivoted from Inbound to Outbound sales, discussing key metrics, qualification methodologies, and sales pipeline stages.

Founder: Chris Flores of C-Flo Consulting, LLC

Chris Flores jumped onto Sales Operations Demystified to share his knowledge and experience in Sales Operations.

 Check out all the other episodes of Sales Operations Demystified here.

You can learn more about:



Tools Mentioned:


Tom: Another very special episode of the Sales Ops Demystified podcast. We’re joined by Chris Flores of C-Flo Consulting. Chris, welcome to the show.

Chris Flores: Hey, thanks for having me.

Tom: Now, we have a super interesting story. Chris joined a startup called Namely early on. Scaled with them, or scaled with their sales department over five years, and has some really impressive numbers that we’ll talk about in a minute. Since then, has done various other things, but now is running C-Flo Consulting, which, essentially, is a consultancy, consulting on sales departments and celebrations. We’re going to get here in the next 20 minutes or 30 minutes, experience from Namely, the Namely journey, but also experience from every other sales team you’ve been exposed to in the consulting work. I’m super excited to dig into that. Before I ask the first question- No, actually I’m going to ask the first question, how did you originally get into sales ops?

Chris: It’s interesting because when I first started out at Namely, which is my first exposure to this world of sales development, sales operations, I was the fourth employee in the first SDR. That was back in June 2013. It seems like a very long time ago. At that moment, as the first SDR, I also was involved in buying Salesforce and all of the sales tools, and I was also the admin. When you’re so young, and you’re only four or five people, and you’re scrapping, and you’re owning everything. It was a natural progression for me to- I always wanted to be in some type of management role.

As an SDR, I’m working with the SDR management, but I continue to own all things operation. I was the owner of sale systems, optimizing things, and buying and negotiating prices with other vendors and whatnot. I learned a lot from it. That’s how I got my start in sales ops.

Tom: Okay. Quick question, you were employee number four, what were the other– In which departments were the other employees from?

Chris: Yes. We had our founder, head of engineering, and marketing. We had those early on. There was so much overlap too because it’s so small and scrappy, and we’re doing everything. Helping each other whenever we can. In a few months after I joined, I remember that’s when we raised to series A. We were to hire more, get our own office space. Start buying more technology, which is always fun. Start hiring more people.

Tom: Good. Quickly, while we’re on that, fast forward to the end of the Namely journey, because that was five years. You were [inaudible 00:02:58] head of sales development, but what was the size of organization on the side of the sales organization at that point?

Chris: Yes. I helped scale that company from me being the first salesperson to at least 100 sales members. We had the team of 30 SDRs, a team of at least 60 account executives, there were pre-sales, sales engineers involved as well, and then managers all across the nation. Not just in New York where we started, in Austin, Georgia, in Atlanta, in Seattle, LA, and San Francisco as well. It’s pretty big sales org. Since leaving, I still try and keep in touch. I’m rooting for them, because, also, I have equity, still, for sure. I think it’s been a wild ride to see the ups and downs of Series A, Series B, Series C and building an entire sales organization from that.

Tom: Got it. The size of the sales operation function when you left.

Chris: Yes. When I left, it was, I’d say, it was around three or four. There is sales ops that worked very closely with marketing operations, as well as an owner of all [unintelligible 00:04:12] market operations, and then on the C level side, or a VP level, we had a VP and revenue operations. We saw a business operations function being built out as well, but sales and marketing involved under one umbrella in what we called, back then, this revenue operations.

Tom: Got it. I know the head of revenue operations would then report, I guess, into [unintelligible 00:04:40] revenue.

Chris: Yes. The chief revenue officer and then directly to the CEO. It was actually a really good alignment because what we learned is that we should never separate sales operations, and marketing operations, and then customer success operations, because they’re all tied to the same numbers in one way or another, in terms of that one KPI, of ARR, MRR, just revenue in general. Having that all rolled up into that one revenue operations role was pretty effective.

Tom: The head of revenue, did the head of marketing and head of sales report to him, or did they also go into the CEO?

Chris: Yes. In that relationship, they reported to the CEO, but it was like everyone’s on the same- They’re working in parallel, as far as how they kept their relationship going.

Tom: Got it. The next question we normally ask is about sales ops tech stack. Now, I assume, correct me if I’m wrong, that you wouldn’t have a mature sales op tech stack C-Flo Consulting. Tell me if I’m wrong.

Chris: No, you’re right.

Tom: From your experience, either at Namely or from other clients that you’re working with, what would you say is best practice, what are the tools that you would need to have functioning sales operations?

Chris: Yes. For sure. You probably heard this from everyone you’ve asked the question, from a CRM perspective at Salesforce, if you’re not on Salesforce, then, especially as a consultant, I will push you to go onto Salesforce, if you want to become a world-class inside sales team, in my opinion. From a prospecting perspective, my favorites is LinkedIn Sales Navigator, ZoomInfo or DiscoverOrg, I know they’re one company at the moment, very powerful contact data, it’s one of my favorites too, so I always recommend.

Then, in sales engagement perspective, I like either Outreach or SalesLoft. They go neck-in-neck depending on the size of the the company, but they’re very strong tools. I’m very familiar with them, and the reps that I’ve trained, they typically always have really positive feedback on that end.

Then, there’s always a data management piece as well, as part of the sales stack. One of my favorites is a company called InCycle which helps with managing duplicates, cleaning Excel spreadsheets, importing, exporting, not just between spreadsheets and Salesforce, but also like HubSpot, Marketo and other tools that you have within your stack. I think that data management piece is super important to have something dedicated to that, which, in my recommendation is always InCycle, it’s powerful.

Tom: Got it. That leads very nicely onto the next question which is about dealing with data quality. We have this tool here that, I guess, can retroactively fix data problems,

but what else do you recommend to clients [unintelligible 00:07:43] Namely to improve data quality generally?

Chris: Yes, you’re going to need an owner, first of all. I’ve seen, and this happened at Namely very early on as well, and a lot of my clients, where it’s marketing is in charge or sales operations is in charge, or they give it to the IT person because nobody wants to deal with it, because it’s just so messy. It’s a pain, it really is. I love data. I love dealing with it and doing whatever it takes to fix it. You treat it as a cadence, whether it’s every month or every quarter, you need some type of dedicated resource and some type of tool where you have your duplicate checks, you’re making sure that AEs and SDRs have the right amount of accounts, they are in your target market, all of these types of things. Like, let’s clean up our room every single month. Let’s clean up our space every single quarter. That’s super important. When I typically go in, I’m pretty much the person who owns it, and I keep that under the umbrella in sales operations because we also know what type of data we want. Marketing can help, and, of course, they will know, but sales is actively engaging with it. They take inbounds, they take outbounds, and it’s something, I think, we can control.

Tom: Do you think sales ops team should be responsible for data quality?

Chris: Agreed, yes.

Tom: Cool. Moving on to buying or getting the sales team to do something that you want them to do. Do you have any tips or best practices around that?

Chris: Force them. [laughs] Force them to do it. No exceptions. I’ve been through a lot of tech implementations and ripping things out, replacing, or getting something new. I think the best is when you have a team that- Like, at Namely, for example, we had a benefits brokerage division. There was a lot of these old-school benefit brokers, have amazing experience in benefits, but Salesforce is blowing their mind. These reports are blowing their mind, and sales engagement tools, so that was always fun. Those are the easiest ones.

Then, the toughest guys and gals are the ones where they’re used to using a specific tool, they’re comfortable, we’re creatures with habits from a sales perspective, and it’s hard for them to adopt something new. What I do is, one, I get them involved early in the process, give them as much of a heads up as I can.

I would involve them in a pilot, if that’s possible, with a specific vendor, get a few champions involved, find out who’s the loudest person in the room and get that person involved first and early, but also show them the data. Now, we’re a bunch of Millennials running companies, which is great, and numbers don’t lie and we understand that.

It’s important for me to show them, ahead of time, before we adopt a brand new tool, or we implement a new tool, that this can work, and hear the numbers. Numbers won’t lie for you. I think, one of the key things that people that I work with forget as well is that if they don’t do all of the above, at least, if you disagree, at least walk away with an agreement to commit.

If you’re disagreeing on the tool, if you’re disagreeing on a new process, at least tackle that head-on with those specific reps or managers and say, “Can we at least agree that we’re going to commit to this for the next quarter? If it doesn’t work, then, all right, we’ll go back to the drawing board.” I think if you follow that type of process, like, I’m a big checklist guy, if you follow that every single time for a new tool or process, then you’re good.

Tom: Got it. We haven’t actually heard that before about, even if you don’t agree, we can still get people to commit for a specific period of time just to allow you the time to see if the data does work out, so you can then convince them with the data. Just writing that down. You must have on-boarded a vast number of new reps at Namely. What are your best practices for doing that?

Chris: Yes. [clears throat] I’ve on-boarded a ton, and have learned a lot. Especially as a first-time manager, one, understanding what it means to become a manager versus an individual contributor, and not really hiring yourself, but hiring that person for the right skills, and the right talent, and the role. There’s culture add, there’s coachability, adaptability to all these different KPIs.

I’ve also made some wrong hires, right? I’ve made some hires that didn’t work out, whether it’s like during the ramp period, or the year end, and it just wasn’t aligned. From that perspective, what’s super-super important is their first two weeks when we talk about on-boarding. I love the quick and dirty two week on-board, but what’s super important is just the reinforcement of training as well.

Sometimes I forget about it as well, it’s just one of those things where, if you’re fast-growing, and you hired your first SDR, your first AE, as your hiring manager, as the CEO, you want that person closing deals right away, but it’s never going to work that way. You have to give them time, you have to give them all the right tools and resources, but also, reinforce it a week later, another week later, and keep going, I think that’s super important.

I like to overwhelm all of my reps for the first two weeks. Because they’re also hungry, they come in with that new hire energy, they’re hungry, they’re ready to go, but the reinforcement training is super important. Also, if you have the luxury of having other reps involved, you have team leaders, if you have SDRs that are veterans, or Account Executives that are veterans, involve them in the on-boarding process as well. Have them shadowing, and running, prospecting, tips and tricks, best practices, doing demo side by side, run demos parallel, whatever it may be, that’s super important.

If you screw up the on-boarding, it’s like screwing up your GPA in college very early on, and you’re playing catch-up from a very low end, trying to get back up to the top. It’s a tough thing to do, it’s a grind.

Tom: Yes. Moving on to sales forecasting. Do you have any best practices for building an accurate forecast?

Chris: Yes. I think it comes down to first making sure that you have the same language amongst SDRs, AEs, managers and in C level. That’s very important because what the CEO may see, or what the VP of sales might see or say, could be completely different. I see the breakdown in communication all the time. Understanding what the stages are in Salesforce, as well as what the probability per stage looks like. 10% for first stage, 30% for second, 40%, 50%, whatever it may be. Once you get that nailed down, then it’s a lot easier to figure out what’s upside, what’s commit. It’s like a swing deal.

The way I like to simplify things from a forecasting perspective, if I’m an account executive, and I go into a meeting with the VP of sales, I want to be able to tell that person confidently what can I close this month or this quarter, what do I think can come in, what’s my upside, what’s the best case scenario, and then, what are the one or two deals that, if they happen to swing in, then I can knock out my quota out the park. That AE should be able to see that within Salesforce, as well as the VP of sales.

I think it just comes down to data, and it comes down to speaking the same language, and understanding that what you tell me is reportable, it’s in Salesforce, you’ve updated it, we’ve maintained it, and my CEO can see it, my VP of sales can see it, my ops guy can see it as well.

Tom: Got it. Quick question from the audience, we have Zach. How do you approach the process of filtering leads from marketing to sales?

Chris: From that perspective, it’s all about the types of fields that we use. My favorite marketing automation at the moment is HubSpot, and aligning that with Salesforce. One simple way to do it, it’s everything that comes into Salesforce, from a marketing perspective, we treat those as leads. Then, everything that comes in from outbound, and our SDRs and AEs are practically going out, I actually have them create accounts and contacts.

We do an account-based sales or account-based marketing model. That’s one easy way. Also, by source. There’s plenty of automation that you can build in. As the leads enter the system, you tag them as inbound, you give them their appropriate lead source. You train your outbound sales team to do the same when they’re creating contacts. There’s a lead source for outbound, there’s specific account sources and whatnot. You build the playbook around that. You get everyone aligned from the on-boarding, just like, “This is inbound, this is outbound.” That’s how you’re able to create that filter and follow in. It makes the reporting a lot easier, in my opinion, too.

Tom: We currently here, we use Salesforce and Copado as marketing automation. Copado is owned by Salesforce. That integration is pretty tight. I actually, like,

[unintelligible 00:18:00] I’ve never actually used it, but the brand is amazing. In that integration between [unintelligible 00:18:07] and Salesforce, have you ever had any issues integrating the two, or is everything all good?

Chris: Yes. I think, early on, definitely. I’ve just finished up HubSpot implementation for a new client, and getting the forms on the website, it’s a bit tricky. I’m not a marketer by trade. I’m more of a sales ops, and on the sales side in the Salesforce. Once you figure out all the kinks, then it’s fairly easy. I have heard that [unintelligible 00:18:36] because they’re so native and built into Salesforce that makes it a little bit more powerful. I haven’t used it at all, actually, but yes.

Tom: Yes, I’ve been keeping it away. [laughter] Making sales reps productive. Thoughts?

Chris: Yes. Early on, it definitely starts in the on-boarding. I like to give, in my first two weeks of on-boarding too, there’s always homework, there’s always something that they can be doing. When I know I made a really good hire, if I’m a sales rep, or I’m an inside sales rep, I’m an SDR versus AE, it’s the ones where I fill up their calendar every single day, and then, at the end of the day, they always ask for feedback, or they always ask, like, “What else could I be doing?” I love that, even though we’re overwhelming them with so much. Every week, within their onboarding process, or every day, I also give them some homework, which is like building up your pipeline, cleaning things up.

“We’ll give you 500 brand new accounts to start with, start prospecting into those accounts. Start thinking about messages,” because you’re going to do this anyways, so do it. Getting them used to the fact that you will always have action items after you have a meeting with your manager or me, so that we’re always pushing and moving forward, that’s the best way to keep them productive. Then, now we fast forward to three months, or six months from now, twelve months, especially if we focus on the SDR function. SDR is a life cycle. It’s what? 12, 14, maybe 18 months, if you’re lucky.

When I was in SDR, I did it for six months, and I wanted to kill myself because I was like, “I want to be a manager.” I was young. I see the upside at Namely, I want to make more money. I want this. I want to go, go, go. Also, there was a burnout because every single day, as an SDR, you talk to people who don’t want to talk to you. You’re cold calling, you’re cold emailing, and you’re hustling. That’s what you do, and I love and I appreciate the role. How do you keep Chris motivated back then? It’s, you need to give me more action items, you got to keep me productive, you have to motivate me and coach me through the weekly one-on-ones. Also jump on issues very fast, like the little things. Your job, as a leader, is to remove obstacles, every single day, as quickly as you can, no matter what it takes. I found that I always gravitated towards the best leaders, CEOs, VPs of sales who invest time, and they do that. Something very simple. If I see an AE or an SDR talk to their VP of sales or one of my clients, and the VP of sales is heads-down focused, and doesn’t even look at him while he’s asking the question, we need to change that.

You need to put the computer down, address them, and have a conversation. All these little things are very important. It could be like, “Hey, my Salesforce isn’t working,” or, “My Outreach is down.” “My LinkedIn password expired. I need your help.” Little things you got to jump on. I think all of that involved with motivating and coaching them, and giving them that real feedback can keep your SDRs happy. You can get them a lot more productive, or keep your AEs happy. They’ll be more productive, and they’ll go to war for someone who goes to war for them. I think that’s super important.

Tom: Nice. KPIs. The question I’d like to ask is, if you could measure any rep with one KPI, you can only choose one, which would you choose?

Chris: I would choose new hire ramp time. That’s my favorite. It’s one of the hardest because it varies by company. It’s different by your target market. If you’re an enterprise, it could be longer, if you’re small, transactional smaller businesses that you’re selling into, it could be a lot faster. I want to be able to find what’s the sweet spot. How quickly can I get my account executives, or my SDRs, to hit quota? Not just hit quota for that first month, but to hit it consistently, whether it’s by monthly quota, or quarterly quota.

If I can find out what that number is, and find that perfect formula, then I want to apply that to everyone who comes in. On top of that, typically, when you have someone who hits that aggressive ramp time, and is strong, and can run their own territory, it’s their own business, they’re the CEO of their own company, you don’t really need to sit with them every single day.

You don’t need to babysit them, you don’t need to worry about, “Hey, are they going to get this task done? Are they going to hit their quota?” You get to lay off a bit, but also use them for training, and shadowing, and helping you out as a manager, because you’re going to be so busy. I would pinpoint that to new hire ramp. It’s definitely my favorite KPI at the moment.

Tom: Nice. That’s the first time we’ve heard that one. Final question is, who [unintelligible 00:23:59] has inspired you the most in sales operations?

Chris: Predictable Revenue, Aaron Ross and Marylou Tyler, that was the first book I read as soon as I got the position to work as an SDR at Namely. Previous to that, I was actually in life insurance, I was selling life accident health insurance for a company called Northwestern Mutual, it was like a commission-only gig, I was knocking on doors, I was running into, I was throwing business cards underneath lawyers’ and investment bankers’ offices, just hustle, that’s it. That’s all I knew, it was, pick up the phone and grind. Then, when I read Predictable Revenue, it made so much sense to me because there was a perfect balance of art and science in sales, it was an easier read, and I actually met Marylou Tyler at a workshop that I did. I think it was about a year ago.

She was involved in a workshop as well, and every time I said something, she would echo what I would say, and we were always on the same page, but I didn’t get a chance to hang out with her afterwards. I’d like to close that loop and get in touch with her again, because I think we’re on the same wavelength here. Yes, that’s a favorite book, I think that’s the sales bible that I’m living by at the moment.

Tom: We will link to that below. Let me highlight a few things that I enjoyed. [inaudible 00:25:36] my favorite thing you said I think was people go for war first for someone that will go to war for them. Do you know what I mean? People go to war for someone who goes to war for them.

Chris: Yes.

Tom: Even that one example you gave about [unintelligible 00:25:49] sales like not giving attention to [unintelligible 00:25:52], I think that’s super important. Involving, when you’re trying to roll out a new process, involving the loudest reps can be useful to do that, and then getting the timeline to commit.

Let’s say you have a new process, people don’t really like it, getting them to commit to a fair amount of time to give you the data to then go back and say, “Actually, this isn’t working, and we should do this.” Many insights. Chris, thank you very much, and I would urge people, we’ll link to LinkedIn, and we’ll also link to C-Flo either above or below this video. I urge people to go and check Chris out to learn more.

Chris: Awesome, great. Thank you so much.


Chris Flores of C-Flo Consulting LLC

Chris Flores of C-Flo Consulting LLC