CRO Chris Calkin On Scaling Sales Orgs

Awesome. Okay, so Chris, you have had an amazing career. Over 15 years of experience in revenue leadership. I want to talk about two particular companies that you have been involved with. Census and Circleci. At Circleci, that's where we met. You rose from director all the way to global vice president of sales, growing the organization from less than five sellers to over 50 while also involved in opening up five offices around the world. And this took place over four years at Sensus. Right now you are currently the chief revenue officer and were recently acquired by fivetran. Congratulations by the way.

Thank you.

So you've led sales for deeply technical products selling to software developers. How do you teach non technical sellers to build trust and sell credibly to software developers?

It's a great question. First part is you can't teach everybody. It takes the right mix of experience, intellectual capacity and willingness to learn. Willingness to learn and intellectual capacity were both things I tried to measure in the hiring process. Because even really, really intelligent people won't actually learn the technology if they don't want to. So that's kind of step one is hiring. Step two is enablement and having company investments in enablement. If there is a organizational attitude that salespeople are not technical and shouldn't be technical, they won't be. And I really think that that is an unfortunate approach that a lot of businesses take. And I think it really hamstrings salespeople from being as effective as they really can and should be, especially in today's world. So you need to have that organizational buy in to salespeople are going to understand the products deeply. That then translates to a lot of resources on the enablement front. That's kind of thing too. Just getting the resources. The third component is enabling correctly. Don't just speak to salespeople as if they're a developer and can immediately understand developer related topics. Speak to them as if they're a salesperson. Go through the 101, then go through the 201. And so it takes a good blend of technical understanding and commercial understanding to do that effectively. And then the fourth part is don't leave them the crutch. If salespeople continue to have the crutch, just like in physical therapy, if I always have my crutches, I'm never going to take those steps. And so sometimes you just have to take away the crutches and take the steps and maybe you'll fall. But usually a manager is there to catch them. And so really getting people out there talking the talk helps them get more confident. Over time and taking more and more steps and eventually running with those technical concepts.

You have had over 15 years of experience in revenue leadership, rising from SDR to Manager to direct Director to VP of Sales, to chief revenue officer at companies like Tune, CircleCI and Census and others as well. What's a belief that you had early in your sales leadership career that you've since changed your mind about?

I don't know if you'll love this answer, but one of the main things is not everyone can do it. When I first got into sales management, I thought that it would be very straightforward to hire gregarious, solid communication ability people that had a decent head on their shoulders and would be organized enough to do the job. And I really quickly learned that that was not the case. And the confluence of skills that are needed in order to be effective in sales was vastly more extensive than I had thought. I hadn't given myself enough credit. You know, I thought, you know, this stuff is pretty straightforward and that it would be easy to teach others. And that was not the case. I remember interviewing quite a few people and then being like, wow, why is it so hard to find a great salesperson? I actually think salespeople forget that themselves and that they undervalue their unique capabilities. To be organized, to have effective communication skills, to be cool under pressure, to be persistent, to understand and distill complex topics, to have challenging commercial conversations. Those aren't skills most people have, frankly. And so that was something that definitely changed as I, you know, spent more time in sales leadership.

You have had an incredible career, rising from SDR to chief revenue officer at companies like Tune, CircleCI and Census. What is something that you think most sales organizations measure that doesn't actually matter?

What do I think sales organizations measure? That doesn't actually matter. So I think a lot of organizations measure activity. Activities. Activity does matter. But like any data point, it's really about the context behind the data and not so much the data itself. You know, as a salesperson, I'm sure you know that posting 100 activities could be extremely difficult or extremely easy when all it is is an integration with your CRM, how fast you can upload bulk contacts. You could get a hundred emails out in a matter of a few minutes. And so then there's your hundred activities. And, you know, on the flip side, if you were to do really extensive account research on make sure you were calling someone, giving someone personalized messaging, even in the world of AI, that would still take you longer than that time frame, and you might not get to A hundred, but it might actually be much more effective. That said, even, honestly, even just having that hundred is more than a lot of people do. Even just doing the like generic not very good work is more than what a lot of people do. And so even that gives you some indication that there's a pulse. But I, I think that it's really about the context behind the activity. The other metric that I think again needs to be measured but is all about the context is win rate. So this would be how of my total new business opportunities that I get, how many do I close? And that is very much another metric that can be gained. My win rate could be extremely high as a salesperson, 80, 80%, even if I fail to qualify an opportunity until much, much, much later in the process. And I actually might be throwing a lot of good pipeline in the trash by trying to keep a very, very, very high win rate. And that's something I think organizationally that can be misconstrued because of metric like generic metrics. Right. I could look at my insight partners metrics of best in class tech company win rates and I could just benchmark around that. But really it's not so much the salesperson's ability, it's what is my qualification criteria to get in the door to be an how good is my salesperson at selling that product. So those are two things I think that often lack context and are ultimately very valuable metrics. But not valuable if you just look at it on its own. I agree.

I love it. I'll do two more. You've operated in both product led growth companies as well as sales led environments. What is one mistake that companies make when they're trying to layer sales on top of a product led growth motion?

I think the usual issue that companies make if they're product led growth, but they have salespeople, is they think that those two things are separate motions. There should be a sales motion and a product like growth motion, which is not the case. Same thing if I'm sales led. If I'm sales led, do I think that everything is just going to come from the salesperson? No innumerable metrics. I'm sure Gartner and Forrester have plenty of metrics that show how much research is done prior to a salesperson engaging. And a lot of that research might include utilizing competitive products, utilizing trials, using free free versions of the software, watching YouTube demos. Could be a variety of things that the product actually has an impact on before the salesperson gets to that interaction. Even if it's an Outbound sale. And so the two components should never be separate. They have to be, they have to be integrated well together. So, so that's kind of problem one that I usually see is dividing the two. Problem two is they have the two things compete. So I've seen this in a variety of situations where it's like if the user enters through this workflow, salespeople cannot touch, or if the salesperson is engaged with them here, then they have to do a paper deal every single time. What that causes is it causes unnatural rep behavior which then causes unnatural customer behavior which then reduces your revenue. So it has the opposite impact you never want to have. If you always operate with what's best for the customer in that scenario and you pay and incentivize people accordingly, then you'll be in a good spot. Easier said than done. It's not easy to do, but an easy example would be, hey, if a customer has pay signs up or pays via credit card, not a sales opportunity. So what you might see there is the salesperson who's engaged with this user goes, I'm going to give you a free trial for a much longer period of time just so that you'll sign a contract rather than do a credit card. And you might have actually monetized that customer much faster in that scenario. On the flip side, a customer might want to easily do credit card, but they were sales led. And you're like, no, no, you have to do this order form. And the customer's like, I don't want to do that because that means I have to go back through my finance process and my procurement process. And so that's arduous too. So those two things should not be in conflict, they should work in a complimentary fashion. And honestly, I think the best go to market organizations. That's exactly what they're doing today. That's great. I agree.

I love all that. All right, last one, Chris. What's a non obvious trait you consistently see in top performing sales leaders?

So I don't know if it's non obvious. It's not talked about that much. So it leads me to believe it's non obvious is organization. I don't think organization is typically a characteristic that most people would think of when they think of either salespeople or sales leaders. And frankly, it is absolutely required in today's day and age more than ever. You have 20 plus systems that you're logging into and getting data from. You have all these different roles, right? Xdr, bdr, str, sdr, isr, eae, cae CDA se. Right. Like an incredible amount of complexity within your org and specialization that's now expected because that is best practice, which maybe I have thoughts about, but certainly massive complexity. And then your buyers are also dealing with that same level of complexity. And so if you cannot stay organized yourself and then work to make sure that your organization stays efficient and productive, then ultimately it doesn't really matter how good of a salesperson you are. The follow up won't happen. You'll drop the ball on a customer contract. You will fail to build. Certain percentage of your team won't be trained, trained well. There might be a massive disconnect between one team and the other team. So organization I think is an undervalued trait. It was certainly something that I had to learn. It wasn't a natural skill that I just had on default. But from what I've seen in today's, today's world, that is a very, very core, non obvious trait of a great sales leader.

I'm gonna ask one more.

Okay, sure. Okay.

I recently heard someone talk about how their defining a company as pre LLM company and a post LLM company. So companies that were created in the last three years after the ChatGPT magic moment and companies that were before that. In your opinion, as someone who has been an SDR as well as a chief revenue officer who has been at product led growth companies as well as sales led growth companies, I'm curious, do you think the days of big revenue organizations for post LLM companies are over or do you think we're still going to have big revenue organizations?

Good question. I think that in the short run what you'll have is smaller revenue organizations with bigger revenue operations organizations. I'm already seeing that. So go to market engineer, rev ops leader and other operational and supporting functions. So even within the revenue organization, things like the forward deployed Engineer, which is like the new hot title that's out there, so less of your huge SDR and AE teams, but still maybe equally, maybe not quite equally as big, but still big revenue, operations enablement and general supporting function teams within revenue. So I think because no one will have the ability to use all the all these LLMs figured out, they'll say we don't need to hire a bunch of salespeople because each salesperson could do a lot more. But we need all the supporting functions and these operational functions in order to use these tools. So I think that's the short, short run. I'm already seeing that happen today longer term as these platforms become more integrated and they become a lot easier to use and much more just seamless, like cool. You know, platforms like Glean, you know, are kind of used as the default as OpenAI makes a lot more of its capabilities can integrate it into business then I do think that you have, you have less specialization so you end up with people and teams that are going to be more, more cross functional. So you're not just going to see the SDRA SE exist anymore. I think you're going to have a sales team and it could be like, you know, go to market at and you'll just see people that are, that are kind of all of the things because they will be supported in the back end by all these operational, you know, we could call them agents. Realistically, I think you could have a more efficient org there. How that translates to overall employee headcount for all companies I don't know. I don't know. It feels like it would cut it to be smaller but throughout history I think we've gone through this. This is a little bit of a new one. You know, people were worried about their jobs, you know, in the industrial revolution and so we still have jobs today. They just changed. And you'd like to think that that will happen again but it. I don't think anyone has the answer of exactly how yet. So I'm curious like anybody else.