Interview with Jonathan Bunford, Director of Sales Operations, Ada

12 min read

With experience that straddles sales and marketing ops, Jonathan Bunford has honed his understanding of both sides of the coin. This week, we take a look at my chat with Jonathan, Director of Sales Ops at Ada. We explored the relationship between sales ops and marketing, along with using OKRs to measure success and how to turn insights into actions. His passion for sales ops became immediately apparent, and I knew this was going to be a good one. The interview began…

Rory Brown (RB): Can you tell us more about Jonathan Bunford and your career to date?

Jonathan Bunford (JB): I started in sales at EventMobi. During my time there, I took ownership of Pardot, the marketing automation platform. I helped with the implementation, which essentially transitioned my role from being sales focused to being operations focused. I then did this hybrid role for a while where I was sales and marketing operations. I found it a lot to manage at the time– especially for the size of the startup when I was there.

I joined Influitive three and a half years ago in a sales operations role where I was able to really focus and double-down in that area. I was working alongside multiple VPs, providing them with the insights that they were asking for as well as finding other interesting things to help them drive the business.

I was there for three years and joined Ada in January.

RB: Awesome. Interesting that you have come through the marketing route. Was it a conscious choice to move to sales ops rather than marketing ops?

JB: It was. In marketing ops, a lot of my time was focused on building and testing the HTML for the various campaigns and working on our website. Though that was really educational and challenging, I found myself more interested in the sales metrics where I simply didn’t have the capacity to focus my time.

RB: Where does one begin in terms of getting the right insights, and how we turn insights into action?

JB: That’s an interesting question because in some cases, the VPs (or whoever is coming to me with the question) knows what they are looking for. It might be as specific as which market, which segment, which industry should we focus our efforts in? In other cases, it might just be, “Why did our close change?” There could be multiple reasons why. It could be an aspect of our process we recently changed, or go all the way back to where prospects originally entered our pipeline, highlighting a misalignment along the customer journey.

The scenario I enjoy most is discovering bits of information that just jump out at me or look a little interesting. In some cases, it is a matter of me going to the leadership team and saying, “I’m noticing a trend here”, or “I’m noticing something that we might want to look into more.”

RB: And given the personalities that you experience in sales and business leadership, have you found any particularly tactful ways of presenting your findings?

JB: Oh, for sure. It is always hard when you are going to be presenting something which puts someone or a whole team in a bad light.

I always give people the benefit of the doubt. In some cases where perhaps there has been a lack of training, or a process issue, or somebody is just not following our processes, I always look for the other side of the story. So when it comes to a lot of the data analysis, one of the things that has been integral for my process as a whole is telling the story through data, looking at the leading indicators: what are the tasks, emails, phone calls, meetings that people are doing on a regular basis, and how does that influence their forecast, and how does it influence their closed deals?

And if I have somebody who is not closing any deals, I look at their activity. Are they putting in the effort but not getting it across the finish line? I had one individual, a strong closer, but with very few emails and calls, the data suggested he had a magic touch to moving deals across the line but the reality is that it was a technical issue where the systems that we were relying on to log their activity had stopped working. You have to dive into what the systems and issues could be before making a conclusion.

RB: You have done two or three different roles like this now. Do you find there is a best practice, or set of metrics which all your discovery and exploration should centre around? 

JB: It all goes back to what I was saying about the story of the data. I categorise things into three buckets. First, there are the leading indicators of the activity, the work that is going in. At the end, are the lagging indicators which is the Closed Won deal, how much revenue are we seeing. In the middle are the movement indicators.

What I have found is in most cases, if I can’t pinpoint a metric it to one of those categories, it is really hard to get buy-in from anybody else in the organization. It might be important. It might be something where I instinctively know there is value but, at the end of the day, if I can’t pinpoint how that metricis going to impact activities, the opportunities movement throughout the pipeline, and ultimately the deals bringing in revenue, I am going to have a really hard time getting buy-in to implement a whole new process or to spend the time digging into information.

RB: That takes us to a nice next question then. In a well-oiled CRM – if they exist – there is a lot of data. In all that noise, how do you know where to go to find stuff that is actually effective?

JB: That is a good question. I can speak specifically to the role I’m in now. One of the biggest challenges joining a new organization is finding out what information there is and whether it’s reliable. We have fields in our CRM that instinctively should be very valuable, but they are not filled out. And if you start trying to rely on the data, but the data is not there, or it is not reliable, you are going to have a problem. So a lot of it has been based on just doing a data check: finding out what is there, where does it come from, who populates it, how often etc.

Then from there it is also a matter of building out streamlined processes to get that information. For example every company wants to know the metrics around their competition, what deals are at risk from competition, who they are beating and who they are losing to. You need to build that into the sales process in a way that doesn’t interfere with the sales reps flow. You want data but equally, the sales reps can’t be filling out new fields every 10 minutes. There is a balance. You want as much data as you can get but you need to make it make sense to your reps. If you go to the other extreme and have no field requirements, you should just assume it is not going to be filled out.

It is a real delicate balance between making data requirements a natural part of the flow or making it a show-stopper – a big flashing red light – ‘You can’t pass Go’ until you fill out this information. There are a few different ways of approaching it. But to then know what is impactful you really need to understand the business and business objectives – whether it is from sales specifically, or from other departments like customer success, or product or the organization as a whole. What is the organization striving for, and what data do we have to help them push that story along?

RB: Can you tell us more about the relationship between the business strategy and building that data into the sales process?

JB: One of the things I really enjoy about my role at Ada is I have a really powerful voice in the organization for these processes.

Over time my confidence in that area has grown, whereas I used to be a Yes man, now I’m much more comfortable pushing back and asking a lot more questions.  Why do you want this?  What is the point? What is the story? How does this impact the growth of the company? And it is not to challenge them, but rather to get a better understanding.

Then with that perspective, we can build in these processes and have alignment across the leadership team. When I am implementing something that I know the reps are going to have a bit of an issue with, I have the leadership team saying a consistent message, “We understand that this is an added step, but we really need you to fill this out; this is why.”

RB: Yes, fantastic. How do you manage the typical ad hoc requests that sales ops are often bombarded with and make sure you are still working towards the company’s overall goal?

JB: It is a combination of experience and confidence. I have worked with some leaders that have really creative ideas and come to me saying “I need this yesterday; it needs to be done.”

I can remember dropping everything I was doing, then getting that project done and feeling proud. But when I presented it to them the next day, they ask, “Sorry, what is this?” It was just a fleeting thought that just popped into their mind, and I doubled down and built it out.

And so now, as I was mentioning, there is a lot more question asking involved. A lot of time people don’t understand the work that goes into the request.

One thing that I have worked on is providing some visibility into what I’m doing. Though I’m technically sales operations – and at the end of the day I report to the Head of Sales – I do a lot of work with other teams because I, like most sales ops individuals, also manage Salesforce and the CRM, so I also get requests from product, from our CS team, from our BDR team, from our marketing team.  At the end of the day my mandate is to support sales, but also ensuring that I’m doing my part to help drive the success of the business and to communicate that across the team. I still say yes to more projects than I should, but I do a much better job letting the team know the time scale and where my priorities lie.

RB: The next question is going to be around marketing. You said you covered sales and marketing ops. How was that experience?  It is two CRMs isn’t it – trying to tie them together and make them all flow – make it all work.

JB: Yes. It was a lot of work and definitely a very large learning curve for me. When I was covering both roles, Pardot was the marketing automation and Salesforce was the CRM. There was a lot of information to learn in a very short amount of time. The few things that I can say today that I value from that time would be having a better understanding of the full journey the customer goes on. It is very easy to get pigeonholed if you have only worked with one team or if you don’t have the benefit of having a revenue ops team that can meet together. And when you’re focused on a single department you can end up hurting another, because maybe you are not focusing on the right deals that are closing, or if there is a misalignment between marketing and sales, then you are hurting that customer’s journey and their path into your sales funnel. So having an understanding of the bigger picture is definitely helpful. 

I also find marketing gives you a different view of the data: Who is coming to our site? Why are they coming? What things of interest are bringing them there? What are people looking for? And then fast-forward. How do we then sell based on the thing that they were looking for? How does their search or the ad they clicked on align with our sales process? How does it align with what we are discussing and the different content we are providing them during the sales process? It is important to look backward and question why we are talking to them in the first place, what can we do to help marketing bring in better leads but at the same time, how do we honour those leads as they are coming through? Ensure our messaging aligns with what brought them to us originally. Otherwise you are disrespecting your prospects and wasting their time. So there is a ton of that passive style data which is really interesting to dive into, which I really enjoyed about the marketing side.

RB: In marketing and sales, there is the inevitable moment where the leads move from marketing to sales. What best practices have you seen for making that moment as seamless as possible?

JB: It’s important to encourage both teams to celebrate their wins. And if sales finds that the quality of the leads aren’t quite as good, you can’t just throw their number out the window, because they are still doing a lot of work to get those leads.

I can say I have had the benefit of working at two organizations that have really honoured and put transparency and communication in the forefront. It’s about encouraging that open dialogue but backing it up with data. For example, being able to say, “we are finding a lot of the new leads are disqualified because, once you start talking to them, none of them have budget.” or, “they found the content really interesting but that article doesn’t signal intent to buy.” By being able to put that conversation piece back in, and having it come from the sales team to marketing, you end up getting this feedback loop that is really helpful.

The one area where it becomes really challenging, especially in the startup scene, is a lot of times departments will get hyper focused on their targets. If marketing is being given this higher and higher number, the easiest way to achieve this is to lower what their acceptance threshold is. And at the end of the day, that can start hurting the sales side of things. So you need that feedback loop not just from sales to marketing but also from the organization back to their investors or to their ultimate decision-makers.

RB: Have you seen good ways of aligning teams or giving them common goals or objectives so everyone is working towards the same thing? What have you seen work?

JB: At all three startups I’ve been at we have used OKRs. I can definitely say it hasn’t gone perfectly at all of the three! It is a learning curve, especially if it is not part of your natural process. One of the benefits of using OKRS (assuming you don’t over-engineer it) is it provides clear visibility across the organization.

Discussing key targets company-wide opens the door for really interesting conversations, and is a helpful way to keep organizations, teams and individuals all aligned.

RB:  Brilliant. A couple of people have spoken about using OKRs and sales ops in different ways and I think it is a really good concept. 

JB: Sometimes it can be a little nerve-wracking thinking that you are responsible for a number, but that is normal in the world of sales. In sales, you have a number and if you don’t hit that number, we have to talk about it.  It should really apply to everybody. It is just a little harder sometimes in an operational role.

RB: So key results you are talking about there are things like speed, average sales cycle, average time to onboard. What sort of key results have you seen which you felt comfortable with as a sales ops person?

JB: For me, one of the big ones is the sales cycle. I’ve seen suggestions of some really wide ranges of how that can be impacted by sales operations. Certain parts of the sales cycle are out of your hands as an operations individual. I have had quarterswhere I have had a sales cycle goal, and although I may have missed the actual goal, I know I made improvements to make the process easier.

And so I feel like it is not only a matter of holding yourself accountable to a target, but also telling the organization that this is a target that you are aware of, and looking at closely for that quarter. And you are doing something about that number as best you can.

I really enjoy training related OKRs, things to empower the team. Everybody who joins Ada in a role that uses Salesforce gets a basic level of training.  But at the end of the day, when people want complex reporting they will come to me. So, one of my OKRs this quarter is to roll out advanced report training. Then a key result would be to decrease the number of report requests by a percentage. Or ensuring that a certain number of people have been trained.

RB: Do you have any tips for sales ops quick wins or, if you are into marginal gains, knowing what to chip away at first?

JB: More often than not, I’ve found the last stage of the sales cycle is typically the longest.  Whether that is creating the order form, getting legal buy-in, making sure the contract is correct, and ensuring it’s all properly tracked in Salesforce.

So that’s the part I focus on first, making it as quick, as seamless, as painless as possible, but in a way that is also scalable and accurate. At the end of the day, we want to have as much information in the CRM as possible, but you don’t want the reps feeling they have to enter all this information just to close the deal.

Depending on the procurement process you can sometimes make pretty significant changes to the sales cycle by helping the sales team align more closely with their champions.

RB: You say that a lot of those days can be cut by actually making processes internally better, rather than influencing necessarily the customer side or is there a bit of both in there?

JB: Definitely a bit of both. It depends on the lay of the land. I think it is easier to make those internal changes. The external ones are tricky because you want to make sure that you are respecting the people you are talking to. In some cases the person you are speaking to – that champion who you have been talking to for months – might not know the legal requirements, or technical sign-offs needed to move the deal forward. So the best advice that I have seen work is getting the reps to start asking those questions earlier in the sales cycle. Before you are actually at the point of drawing up a contract, ask your champion to talk to their legal team. A way to approach this is to ask if they can set up a call between the two legal teams. Sometimes the buyer has no idea of what is involved, so by pushing for that conversation you are respecting your prospects time and helping them look even more prepared to their team.

RB: A couple of light-hearted questions. What would you say is your favourite and least favourite part of sales ops?

JB: I love the technology, the automation, knowing how the domino effect works. I could eat that up all day. I absolutely love it.

My least favourite would be some of the expectations, especially being a new person in an organization, and managing the CRM.  There are times when people assume you must know everything that is in Salesforce because you own Salesforce.

RB: You mentioned that you work a lot with your VP Sales / Head of Sales. Looking at that relationship between sales ops and sales leader, what famous duo would you say best represents that relationship?

JB: I’m not sure why, but Calvin and Hobbes immediately came to mind. The relationship between sales ops and sales leader is a close partnership. I can say that I have always felt as though with my sales leadership I don’t feel like it is a top down relationship, it is definitely a partnership, even though at the end of the day I report to them. At the end of the day I genuinely feel it is a partnership, in that their success is my success and vice versa.

RB: Wonderful. It’s been a pleasure, Jonathan.

JB: Likewise!

Want to get more insights from sales ops leaders? Check out our other posts in the sales ops interview series.

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