Share this article

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

Related Content

Analysis of $54 billion in revenue: Insights from the 2024 B2B Sales Benchmark Report

Navigate the changing B2B sales landscape. Expert insights from the 2024 Benchmark report guide you towards improved win rates, shorter sales cycles, and lasting customer relationships.

Crafting an Effective Sales Kickoff with Jennie Drimmer, CRO of Thomas International

Jennie Drimmer, CRO of Thomas International, joins the Revenue Insights Podcast to share strategies for crafting effective sales kickoffs. Learn how to focus on big themes, communicate business impact, and drive results in any economy.

Effective Leadership, Evolving Go-To-Market Strategies, and Self-Sourcing with Chris Elliott, CRO of BizLibrary

Discover Chris Elliott's strategies for maximizing seller performance within today's buyer-driven sales environment. Learn how self-sourcing empowers top performers, why understanding buyer journeys is vital, and how to foster a high-energy work culture that boosts sales success.

Director, Sales Operations: Jonathan Bunford

Jonathan Bunford jumped onto Sales Ops Demystified to share his knowledge and experience as the Director of Sales Operations at Ada.

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

You can learn more about:



Tools Mentioned:


Tom: Joined by Jonathan Bunford who is currently director of sales operations at Ada. Did I pronounce that company name right, Jonathan?

Jonathan Bunford: Perfectly, yes.

Tom: Jonathan, interestingly, has previously, before moving in sales ops, has experience in marketing operations. Hopefully, we're going to dig into that. Since then was sales operations manager and senior manager at a company called Influitive and is now directing sales operations at Ada. Jonathan, welcome to the show.

Jonathan: Thank you very much. Thank you for having me.

Tom: Let's kick off, and maybe we'll cover the marketing operations part here. How did you actually get into sales operations in the first place?

Jonathan: I joined my first startup in a sales capacity, and like many startups, I wore a million different hats. One of the responsibilities that I volunteered for was implementing part of the marketing automation platform. At that point, my entire career path changed. I left the sales world, focused on marketing. That meant I was owning Salesforce and Pardot and the integrations and making sure that the data was passing back and forth properly and a lot of the different responsibilities that came in both worlds.

That was my introduction into the operations area. Then from there, it just doubled down. I felt a lot more passion about the sales idea of things, the sales metrics and also just the power that can come with some of the tools that are in the sales camp. It just doubled down there over the past couple years.

Tom: Awesome. Interesting thing you say that, because we have someone in our team who helps a lot with these podcasts and webinars, is called Josh. Shout out to Josh. Now, josh is responsible for our incidence with Pardot, but I actually hadn't thought of Josh as being in marketing operations. Maybe I'm wrong. I thought Josh is the marketing automation manager. Which is how--

Jonathan: [chuckles] It goes back to that idea that we were such a small team. I maintained everything from the actual automation platform, the automations that took place. Building up the HTML, templates for the emails, working on the website. There were a lot of different pieces that I was involved in. The umbrella of just marketing operations and the entire tech stack for marketing fell on my shoulders at that time.

Tom: Got it. Then you expressed more of an interest in sales. Did you move into a more sales like operations role within that same startup or did you- was that when you moved into a different company?

Jonathan: I balanced both worlds while I was at that first company, it was EventMobi. It's a lot to manage. The marketing scope is huge. Sales is huge and trying to manage both of those was really challenging. When I began to look for another opportunity, I decided that that could be a good opportunity to focus on one area of the business. Between the two, I really enjoyed, as I said, I really enjoyed the sales side. That's where I chose to put a lot more of my focus.

Tom: What was it about the sales side that drew you to that and away from marketing?

Jonathan: That's a really good question. For me, the part that I really enjoy about the work that I do is the technology, being able to build out processes and the automations and the behind the scenes of the business. I found that, at least from my perspective at the time, I found that there was a lot more potential in the sales area than there was in marketing.

I found that, at least with the marketing side, I felt pretty comfortable. It was also a good opportunity to grow a lot more, where it was, if I'm hungry to learn something new, I'll get that option, that opportunity by focusing in sales where I had some experience, but not as much as I had on the marketing side.

Tom: Was that business B2B or B2C, just out of interest?

Jonathan: It was a B2B business. A lot of the organizations that I work for are ultimately B2B2C. You end up having two sets of clientele that you need to worry about. There's your customer who in turn has their own customer to worry about and how you manage the expectations across both tiers of that.

Tom: Got it. First of all to Ada, what are you currently using technology-wise in the sales part of the business?

Jonathan: Salesforce is our CRM of choice. I build a lot of our processes on top of that. Another major tool that we use is Gong, which does the call recording and a lot of analysis behind the scenes, a really fun tool, if you've never checked it out, it's a lot of fun to see the data that they can pull from a conversation. We also have a few tools that we use, depending on which team. It was mostly a budget decision, but, for example, for email, in terms of automation and logging, we have Outreach for our BDR team. Then we have Groove for our sales team, and then for our data tools, we have DiscoverOrg for our BDR team and then Zoominfo for our [unintelligible 00:05:32]

Tom: Interesting, and just for the audience, what's the ratio of people within the sales operations team against the number of BDRs and [unintelligible 00:05:44]?

Jonathan: One to everybody. Right now I'm a single man show, and so it's a lot to manage in terms of making sure that all the teams feel that they're getting the attention that they ultimately need. That's where having a great organization where they understand that there are- at this point we have between 15 and 20 BDR and sales individuals. They understand that it's just me, where in the past I have felt as though I'm getting pulled in a dozen different directions, I found that they definitely understand that I am helping a number of different individuals and so it's a lot of prioritization to ensure that each team gets the attention that they ultimately need.

Tom: That way, when they come to you with those tiny little Salesforce customization request, you will push to the bottom of the pile.

Jonathan: Exactly. Sometimes it can jump up higher if it sounds really fun and then I just say I'm really excited to work on it, but more often than not, it's what's the organizational objective, that's what gets the most focus and then working its way down the priority chain.

Tom: A lot of people that come on the podcast say that one of the crucial skills you need is management of those stakeholders, so the sales reps [unintelligible 00:07:05] but also the VP of sales and the CEO.

Jonathan: Absolutely.

Tom: It's been on this place. Let's talk about data quality, is that your responsibility?

Jonathan: Part of it, yes, so as I mentioned before, we have two different data pending tools, we have DiscoverOrg and Zoominfo, which really are now just one organization now after the acquisition. We have a few other things that happen behind the scenes when new leads enter our system. What we have found is that, for our business, primarily, a lot of our success is dependent on certain data points within the support team structure of an organization, what tech stack are they using, how large is their support team, what channels do they get inquiries.

A lot of that information is really hard to find. Some tech stack info is out there, but the quality of it is really hit and miss, and so what we have found is that a lot of the quality data comes from actually talking to somebody at that organization with the Discovery Call. For me, it's building out the processes within Salesforce to allow the team to enter that information and in easy way at the right time, which can ultimately then steer our business focus and help us as an organization prioritize where the business should be aiming.

Tom: Just [unintelligible 00:08:29] Ada is a AI for customer service teams, right?

Jonathan: That's correct.

Tom: The way that you're saying this, it's very hard to get good qualification data from these sources because, I guess, Zoominfo don't know [unintelligible 00:08:41] customers support tickets [crosstalk]

Jonathan: Exactly, and surprisingly, nobody wants to share that information just like a quick email, picking up the phone, having a conversation and building out that relationship early so we can get some of that information as quickly as possible.

Tom: Do you push the FDR's to try and get- on the cold core, do you push them to try and get that information right away or would you say, "Actually, no, let's jump on a Discovery Call to have a bit more of a structured conversation," or both?

Jonathan: Both. A lot of the time that will come up in the first conversation because it's a very quick way to ensure if we're talking to somebody who's ultimately interested or maybe just tire kicking. There's nothing wrong with seeing what the tech stack is out there and what the opportunities are out there, but at the same time, we know that if your support demand is so small, our solutions overkill, it just doesn't make sense if you don't have enough support inquiries or other factors.

The sooner we can get that information, it just creates a better buying experience. Nobody wants to waste their time going through a bunch of demos and then finding out like, "Oh, this is absolutely not a fit and we should have known that earlier." It's just better if we put the cards on the table earlier for that qualification process to move as quickly as possible and then move on to the fun part, the demos and building out that actual use case for the prospect.

Tom: Got it. Let's just focus on the FDR's. If there's something new or some tweak you want to make to the process, how do you go about getting them to be keen about the process, to really want to implement this new change?

Jonathan: For sure. At Ada, the [unintelligible 00:10:35] and the BDR team sits under marketing, so I don't have too much of a say within their processes, but the same question would apply to the sales team. Primarily, what I have found is that you can't just bring in a new process, just tell everybody that it's what needs to be followed and walk away because nobody will do it or they'll just do it to the lowest possibility that they have to.

If you put a new field in and say, "Everybody has to fill this out," if there's no true understanding as to what that process is for, why we're requesting that information, why it helps, you'll find people put in junk information, and so by requiring the right information at the right time and the only way you'll really know that is by talking to the people that are on the field.

Talking to the salespeople, finding out what their pain points are is massively important and then building that process with them involved as closely as possible. If you get their buying in in that when you build something out, at the end of the day I want so much information, but I need to get the sales team bought into why we need this information, otherwise they're not going to fill it out.

Tom: Yes, and that's, I think, like the crucial part. You have to create the interchange of the new process with with the sales team, right?

Jonathan: With them, exactly. In the past when I was more junior in the role, I would try and implement something and the intention was fantastic, but at the end of the day it wasn't successful because I brought it out the wrong way. I didn't bring it to their attention, I didn't get them involved, and so at the end of the day, I'm just trying to add an extra step in the process, they're not going to want to do it.

Tom: We just have a question from Zack. Can you tell us more about the relationship between a business strategy and building that data into the sales process? That question makes sense to you, Jonathan?

Jonathan: I think so. I think what Zack is asking about is when ultimately the business has certain areas where they want to focus, whether it's, do we want to go enterprise, what sort of industries do we want to double down into and then how do you learn that within the sales process? That's something that I'm actually still in the process of ironing out here at Ada, but a lot of it is, there are certain data points that are helpful to drive the sales cycle forward and then there are other data points that are helpful from the business, and it's how do I find that balance.

For example, something like the decision-making process, I personally can't drive a business decision off of how a client or a prospect is going to decide to purchase us or not, but that's something that's helpful for the sales teams will need to build that into the structure of the sales process, when do they learn that information, when's the right time, when's it too early or too late.

Then going back to some of the data that we don't get naturally, looking at the number of support inquiries and the tech stack, it's how do we bring that information which does help the sales process, but as a whole, how do we drive our business behind that? It's all about- whether it comes down to having that sales process broken out into multiple stages and aligning with the team, when does it make sense that you would learn this information in a natural way? Sales is very much a give-and-take experience and so how do we get that information at the right time?

Then it's just sifting through, and then on my end, it's sifting through that data and trying to find the trends, anything from sales cycles. Everybody wants sales cycles to be as quick as possible, but the data that I pulled recently shows that the faster we close, the lower the revenue is. Is that good or bad, not necessarily bad because it means we get them in the door faster, maybe we can grow those accounts out over time. There's a lot of nuances to it, but it's all driving the business decision as to how do we sell, who do we sell to and what industries, et cetera.

Tom: That's super interesting how trying to compress sales cycle could reduce deal size and so they'll see pressure to reduce cycle, but then if it has that impact on revenue and you can then upsell them, maybe you do want a [crosstalk] cycle. [crosstalk] What is the average sales cycle for you guys at the moment and have you tried to actively shorten that or it was just an example?

Jonathan: That's something that we're looking at right now. On average, it's around three months, plus or minus. In some cases, it can be a lot faster, especially if we already have a relationship within an organization. If a sales individual comes on board and they already know people that can drastically improve on the sales speed or if we find that somebody has worked with us before, maybe they've changed organizations, but they already know who we are, they know what we do and so it can happen a lot faster.

Plus or minus, it's around a 90-day mark and we have found that the fastest is around like 30 to 60 and then the longer is around 120 and it shows that the longer it takes, generally speaking, we do bring in a higher revenue target. It's something to keep in mind.

Tom: Cool. How are you currently onboarding new people into the sales team?

Jonathan: We are onboarding like crazy at Ada, we are growing very, very quickly, which is a lot of fun, it means every week we're welcoming new people onboard. There's already the firehose of information that happens when somebody joins the team, there's the technology, there's meeting all the different teams, learning about the product. I come in about midway through all of that and what I personally do is, I'll work them through our tech stack from a very high-level bird's eye view.

These are the tools we use, this is why we use them, and I'll leave it to them for a while for about a week or two because I find that if I sit down and walk through every step of our sales process, every field, every requirement, none of it is going to be remembered at the end of the day. By walking through it from a high level first, letting them sit with it and then- specifically in Salesforce lightning there's now the guidance for success for each stage.

Using that to help tell them and explain to them, "This is what you should be doing at this stage, this is why, this is the information you want to be gathering, these are the questions you want to be asking." All that information can then help teach them when they're ready and then, obviously, I'm available all the time. When a problem comes up, I'm here to help answer that or point them in the right direction.

Tom: Are you currently actively hiring salespeople at the moment?

Jonathan: Yes. Very much so. [laughs]

Tom: You're going to be going, you mentioned, 15 to 20 over the next, say, six months, so you're looking to double the size of the team or you're just adding on?

Jonathan: When I joined Ada in January, if I were to think of sales and BDRs, we had six individuals. Already we've grown quite a bit and if all continues to go according to plan, we're going to be growing even further throughout the rest of this fiscal year and into next year as well.

Tom: Cool. Are you actively involved in the hiring process for salespeople? Do you interview or do you do any from that separately?

Jonathan: I wouldn't say so much on the active side, I'll sit in on the odd interview here and there, but it's mostly the sales leadership and those people that are in the frontlines that will have a better sense as to the different strategies that somebody could bring to the organization. I have been brought into a couple, I do enjoy it, but it's not something that I focus on here at this time.

Tom: Let's talk about productivity, especially if you're growing sales team, if you have a productive process or unproductive process and that's going to be worse, I guess, as you have more of them. What are you going to be doing over the next six months to ensure productivity with new reps?

Jonathan: One of the first things I did when I joined was looked at what data we had and what we were ultimately missing. What I found was- the initial pain point that I found was we weren't actively logging our calls and our meetings as effectively as we should. If we're trying to do analysis on-- We have a 60-day sales cycle or 90-day sales cycle, what does that look like? How many calls does that take? How many demos? That information wasn’t there.

One of the first things that I did was implemented a tool to log those emails, to log those calendar invitations so that way we can see what effort does it take to get a deal across the line or what does it take stage by stage if we are able to drill down that specifically to see what does a normal deal look like, what does a really successful deal look like. Then using those two data points together, we can then use that as a benchmark when we hire new folks.

That was stage one. From there, it’s a lot of what can I do to take the cognitive load off of the team and get that away. A lot of our salespeople have so much information in their minds. I can ping a few people in the sales team that have been here for a while, and ask them about an account that they closed six months ago, and they know everything just off the top of their heads, which is fantastic. That means there's all this mental space that's being taken up holding on to this information. It's, "What can I do within Salesforce, within our process to get that information out of their brain so they can focus on the new deal and they can then put that much more effort into it?" [unintelligible 00:20:26]

Tom: The final point, well, thinking about something that you've done that have been able to reduce the amount of things the salesperson needs to remember.

Jonathan: A lot of it comes down to within the opportunity cycle, within the sales cycle there were a lot of little data points, something as simple as certain aspects of their tech stack, making sure that we were tracking that properly, that we did have fields to track things like competitors, which competitors are we up against or facing within certain deals or what's the tech stack of the company. The actual process of importing that information was painful at the time.

When I first joined, if I had pulled the data from Salesforce about our competition, the data suggested we had no competition because there was nothing there. Then when you actually talked to the team, it was, "Oh, we faced these people in these deals and we've won against these folks and we faced these folks more often." The data wasn't there to hold on to all that.

It's a bit of a painful process to build out something, get everybody to go back in time and think, "Okay, look at the deals that you closed, whether won or lost over the past maybe 6 months or 12 months and just repopulate this information, get it out of your head." It's a bit of a painful chore to get them to go back and to do that, but the idea now is I can now use that data effectively and also they don't have to worry about it anymore and so they can just move on and focus on something newer and more time-specific for what's happening now.

Tom: Got it, taking the information out of the heads of the salespeople and putting it into Salesforce, more of like making that process easier so they'd actually do it. Got it. Let's talk about KPIs, what are you currently tracking?

Jonathan: From what I can think, our KPIs are pretty standard, things like activities, changes in pipeline, growth and decrease, pushes and pulls. When an opportunity is created, we set a default assumption just based off of our sales cycle. We look at how often does that get pushed or pulled, are there any trends to the pushes and pulls, how long things take within each stage and also what are people doing within each stage. When I joined, and still right now we have about six sales stages and there's some discussion as to reworking those a little bit, maybe adding one, maybe removing one.

Ultimately, I need to look at that data and see what's happening, where are the potential bottlenecks in our sales process. That's all through those KPIs. The sales cycle, which we've already talked about, the close rate obviously is a huge one for sales operations. One that I've looked at before, I've looked at in previous roles and I've read quite a bit about is sales velocity. I feel like that's the big thing that a lot of folks are talking about right now. I understand it, I've built out formulas, I built out things in Excel and processes within Salesforce to attract it.

I'm not quite bought into, at least with the organizations I've been a part of, how to make it actionable. A lot of the times what I'll be doing is working on different data points and KPIs behind the scenes, nobody else is really aware of it. I'm not surfacing at any dashboards that are rep facing. Looking at those different data points and thinking, "Is there something useful here?" Because more often than not you can get overwhelmed with data.

What I try and do is hold that data back, wait until I can actually see what the story is and then feed that to our leadership team to say, "With this data point, we can drive the business, we can do this or that and we can make these adjustments." With sales velocity, I liked it, but right now it seems like the basic story it says is either add more to your pipeline or decrease your sales cycle. To me, that's already a given. You want to close things faster for more money and more often.

I'm not really sure what I'm learning extra from sales velocity, but I feel like maybe I'm just missing that last piece of the puzzle there.

Tom: If you could explain sales velocity in one sentence for the audience, what would you say?

Jonathan: I was just about to google the formula, but ultimately, what sales velocity is, is a calculation of, on what frequency usually-- It can be depicted in a daily form, it's every day how much revenue are you bringing into the organization. For example, at Ada, a lot of our business is very hockey stick shaped, it's usually towards the end of the month or at the end of the quarter, which is very common in the tech space, but if you break that apart, it's, if we look at the deals in the pipeline, how quickly they close, the win rate and the average deal size. I think those are the different factors. On average, how much revenue are we bringing in on a daily basis? As you tweak those different levers, you can see that sales velocity increase and ultimately gives you one numerical value to see, are you getting better or are you getting worse at bringing revenue into your organization. It was longer than a sentence, but I think that's [unintelligible 00:25:32] [chuckles]

Tom: Got it. Final question, who has taught you the most about sales operations?

Jonathan: I have a two-part answer for this one. One individual that I learned a lot from was a previous VP of mine David Primer. He is a very, very intellectual individual and just has this way of looking at data and looking at problems from a very unique perspective. One of the things that he helped me learn was being in the sales operations role I sat in on so many sales sessions where I was learning about different sales methods and Sandler and so many different things, but at the end of the day, they don't really apply to me. I would think of how can I build that out for the sales team, how can I use that to drive the sales team seem to be more effective.

It was never a thing that I took on for myself, but what he helped me realize was the sales team are my customers. The same way that you manage expectations with your prospect or you have a sales cycle and you have a champion, all of those things actually apply to me as well. When I'm building out a process, not only do I need the sales team involvement, I have my sales champion, I have the individual that's really bought into what it is that I want to build out. They can help get that excitement with the rest of the sales team. That was huge for me, was realizing I have all this data that's in my head that I can actually apply to my role directly. That was huge.

Then, the second part, because I did say I have a two-part answer, is just a community in Toronto. There's a pretty sizable sales ops community in Toronto. Just connecting with different individuals, whether they are senior or more junior, everybody has a new perspective, a new idea, a new problem that they're trying to solve. Just having people in the area to meet up with, grab a coffee and just talk over some issues and problems, is really helpful and a great way to spread knowledge but also learn something new.

Tom: Is there a name of a meetup group or online group in Toronto that we can give a shout out to?

Jonathan: Actually, I'm in the process of trying to start one. We had one meeting right now and I dropped the ball in June and didn't get it started. Hopefully, in July there will be another sales ops meetup in Toronto, but there's no meetup group or anything yet. It's very, very grassroots right now.

Tom: Fantastic. That concludes the interview, Jonathan, director of sales operations at Ada. Thank you so much for coming. There's a few things I picked up that I want to quickly recap on. Buying from the sales team, I think David Primer's advice to you was absolutely phenomenal. This is what everyone's been saying, salespeople are the customers, we need to get buy-in.

I really like the part about the deal analysis about how you're looking at a perfect deal, if there's such a thing, how many engagements, I think that's very important. Taking the cognitive load away from the sales team and pushing that into CRM. Then, the final one, which I hadn't heard before, which is about you might have all this data that you're producing, but there's no point really showing that and trying to confuse the salespeople with data that you don't really know what it means or you don't have any [unintelligible 00:28:59] That's what I got, Jonathan.

Jonathan: Fantastic. [chuckles]

Tom: Thank you so much for the time.

Jonathan: Thank you very much.


"Compressing a sales cycle can reduce deal size." - Jonathan Bunford