00:00:00 Jake Jeffries: The unique thing about this story — and the big learning for us — was about using sales velocity to help us organize and prioritize the types of things we did within our territory. So top tip for absolutely anybody thinking about prioritization: pull the list of all your opportunities, calculate the sales velocity, pair that with some other type of qualification data so you can get a more complete picture. That will help make it really obvious what you should be prioritizing. The thing that made the difference is that I had a point of view, and I was open-minded to going out and finding out whether or not it was truly correct for my customer. So all those words — implicating the pain, the decision criteria, the champion, the economic buyer — all of those are only important if you are genuinely in a search for the truth, to find out whether or not your customer is going to benefit from engaging with you. And if you can genuinely get to that truth, you have all the power in the world to ask for more, to use that to sell to your customer, to engage with them on their success metrics. And it makes all the other stuff, when it comes to MEDDICC, a lot easier. 00:01:20 Pim Roelofsen: Hey everyone, this is Elite Dealers. My name is Pim. This is another episode and this one has been a long time coming — because it is with our very own Jake, who is now a member of our team. Welcome, Jake. 00:01:33 Jake Jeffries: Hey, Pim. Thanks for inviting me onto your show. I didn't know if it was a prerequisite for staying on the team or not, but happy to be here for an episode of Elite Dealers. Whether or not it was secretly mandated — or if it's just an awesome story that we get to talk about together — yeah, glad to be here. 00:01:41 Pim Roelofsen: To be honest with you, Jake, I think it might be a little bit of both! But can you do a very brief introduction for the audience and then we'll get into it? 00:01:56 Jake Jeffries: Yeah, absolutely. Hi everyone. My name is Jake Jeffries. I've been in enterprise sales for about eight years, and I've been using MEDDICC for about the last four or five. The last four or five have been massively more successful than the first four or five. I actually started my career in sales working in recruiting, before transitioning into tech sales. Now I'm here at MEDDICC — the company — and I joined specifically because I am a huge nerd for all things sales. I love to get into the details of how things work, how to optimize, how to think about best practices, how to scale that up with a team, how to organize your go-to-market team. For me it's been really fun to be here at MEDDICC, helping our customers do exactly that every day. So — here I am. 00:02:35 Pim Roelofsen: I love the positive angle on being a nerd and just obsessing over something to become the very best at it. Okay, so this deal we're going to talk about today — I know there's a little bit of a pre-story to it. Can you give us the high-level schematics? What does the customer do, what was the deal size, that kind of stuff? 00:02:55 Jake Jeffries: Yeah, absolutely. This is a fun deal for me because it was one of the very first and most memorable deals I closed as an AE where I really learned how to call my shot, how to approach a deal with a more strategic mindset, how to think about early inputs leading toward the end. For me this deal was transformational — it was the first of what I'd call the major deals I started to close from then on in my career. So this deal was with a large online retailer based in the north of England. We did the deal at a previous company — Andy Whyte and I, along with the CEO of MEDDICC, who both of us worked really closely with at the time. He was also my leader then. The unique thing about this story — and the big learning for us — was about using sales velocity to help us organize and prioritize our territory. We closed this online retailer for a total contract value of about a million over a two-year deal. It was a major landmark deal for us in Europe, and also really significant because it was the first case study we could use to produce a whole new sector of customers in the region — it defined the region for us, and they remained our largest customer in Europe for quite some time. So it was really instrumental. 00:04:16 Pim Roelofsen: That's awesome. I think with MEDDICC and qualification we typically say something along the lines of focusing on the right things in the right deals — but I guess your story around the sales velocity equation goes back to focusing on the right accounts first. Is that accurate? 00:04:36 Jake Jeffries: Yes, definitely. And one of the top tips I would give to AEs, sales managers, sales ops, territory planners — anyone thinking about organizing a list for the year, or how to prioritize what to do in the remaining half of a quarter — is this: what we did that worked really well was pull the list of all the deals that had been closed in the enterprise segment, in the US and in Europe. We used those raw figures to calculate sales velocity — number of opportunities, multiplied by the percentage successfully closed, multiplied by the average deal size, divided by the time it took. That score was a really interesting insight when you pair it with industry-level data. What industries tend to have really high sales velocity? What size of company, what size of account? Using qualification data beyond just basic size data to organize ourselves around sales velocity — after running that exercise, Andy and I found that in our business, online retailers and quick service restaurants specifically had the biggest return on sales velocity. We had primarily been targeting big banks, financial organizations, major tech companies — Amazon, Apple, all these behemoths. We didn't really recognize where we were getting the best return for our time. Those two industries quickly stood out as the opportunity to go in and do really significant-sized deals. And that's where MEDDICC was really helpful in filling the gaps and understanding the landscape from there. 00:06:50 Pim Roelofsen: I love that. And that really helps toward creating your ideal prospect profile as well, right? You plan for the year, and I think this might be a nice segue into this specific deal. Having done that as preparation and kind of redefined your account set — what was the impact on sales velocity as a result? 00:07:15 Jake Jeffries: Well, our average deal size when I started doing this — when I remember doing Salesforce Day — couldn't have been more than $50,000. The average deal size I was hunting for in my new sales velocity equation was somewhere between $150,000 and $250,000 as the sweet spot. Then there was an additional tier above that where we were really fighting for $500,000 to $1 million. So we had a whole new system, playbook and approach — going from doing any $50,000 deal we could find, down to categorizing and accurately forecasting which $100–250k deals and which $500k-plus deals were going to close throughout the year. Sales velocity was massively impacted not just by performing better, but by having the confidence to know: these are coming in around this quarter, these are coming in around that quarter. Because we could see those process elements ahead of time. 00:08:21 Pim Roelofsen: And I like the sales velocity equation for planning ahead and focusing on the right accounts — but then also, once you translate it to the MEDDICC framework, it's like: if we now understand we need to do a better job at qualifying and building champions, when we do that — how much does it impact sales velocity? So it's something you can use in planning, but also retrospectively. As you start making improvements and look back at how much better you did, you can gear up for the next step toward sales excellence. 00:08:58 Jake Jeffries: Exactly. There are so many factors that correlate to sales velocity — deal size, time to close. But what we found to be most successful is using it as guidance to put ourselves in the right situation, so that at the very least you're selling to a customer who has some great reference stories, a reason to care about your unique decision criteria, a group of others in their industry who can speak to the pain you're solving. And when you approach them, you have a level of confidence already built in. You're automatically going to get higher returns on your time. Maybe not everyone has the luxury of focusing on a single industry — but maybe you call your shot on two or three, build your account strategy around those high-velocity engagements, and repeat those results from there. 00:09:48 Pim Roelofsen: Awesome. Okay, let's dive into this specific deal then — because it sits right on top of the categories you were talking about, right? In that $500k-plus tier. How did it come about? 00:10:06 Jake Jeffries: It started from an interesting engagement. Looking back, there's so much we'd have done differently — but one thing I would not have changed for the world is how this kicked off initially. Our SDR, a gentleman named Yusuf — who has gone on to be excellently successful, he now leads a team at Branch — reached out with a really specific, guided screenshot showing a broken user experience between their social media platform and their mobile app. It was a very personal message, with a kind of flow built in, showing a really clear and unique pain point we knew we could help solve around user experience. And the response to that message was: "Why don't you guys just come down to Manchester and show us your stuff?" 00:10:50 Pim Roelofsen: Great. So you rock up in Manchester? 00:10:52 Jake Jeffries: We roll up to Manchester — this was end of 2019, so in-person meetings weren't totally unheard of at that point. We have this first meeting in this old, slightly janky building, like a warehouse. It's a family-owned business with a historical feel to their buildings — this was definitely before a lot of the growth and updates. So we're in the back room presenting our screenshots and our stuff. What was interesting — and what we really learned in hindsight — is that the business case they were building was different from the one we had in mind. We were focused on user experience and features. What they were focused on was the value the data could bring them, and specifically how they could use that to optimize their own conversion rate. That eventually floated all the way up through the organization to the front page of their board. You only get to understand that through building your stakeholders and getting a champion working with you. 00:12:22 Pim Roelofsen: And shout out to Yusuf for setting this off — I love a story that starts like that. So at this initial meeting, how would you now put the stakeholders into MEDDICC categories? 00:12:46 Jake Jeffries: One of the reasons this went really well is that we met a qualified champion early on — or at least someone with the potential to be a champion — from the very first meeting. That was the person who'd responded to Yusuf's outreach. This person had power and influence. We later really understood that they had a vested interest in our success, partly because our success was the success of their conversion rate — the metric they were wholly responsible for. They were also currently running four out of the company's thirteen or fourteen brands, the biggest ones. They had larger ambitions, and they saw this project as a really good way to drive the solution in the right direction. They were selling internally on our behalf because they knew the other directors. They helped us navigate the executive board. This was someone who had the ear of the family — to enough of a degree that we were able to get our proposal through. 00:13:25 Pim Roelofsen: Sorry — the ear of the family? That sounds like a scene from The Godfather! 00:13:30 Jake Jeffries: Ha! It's not quite that cool. Hopefully they don't hear this. But yes — he was genuinely the type of qualified champion who, looking back, we should have seen from a lot further out. In the very early stages I was still taking a lot of meetings with a lot of people. In hindsight, making sure you double down on the right person is the most important thing in sales, because that deal could have been seen from much further away knowing what we were dealing with. 00:14:13 Pim Roelofsen: That makes sense. And so the personalization that Yusuf brought — that's typically what earns you the right to ask more questions, and starts building a potential champion into an actual one, so they begin coaching you on how to win. Is that a little bit of what you're sensing here — that the use case you prepared for was solid, but slightly different from what they were actually trying to solve? 00:14:38 Jake Jeffries: Yeah, we learned more over time. The important part about those early interactions was that we were building them as a champion by being a good partner to work with. We were willing to travel in person. We showed up very prepared. We'd thoroughly thought through their user experience. We didn't necessarily understand every specific problem they had — and we actually learned a lot more that we used later on. But because this was a new customer category for us, the most helpful thing was showing up super prepared, making sure we were always thinking about how we were adding value at every stage. Because of that, we really bought the opportunity to ask more challenging questions. Those questions started to bear fruit later in the process, when our champion introduced the fact that the data was the most interesting part of the engagement — when we simply asked, "How do we see the measurement of the value of this partnership?" They started talking about the value cases, gave us a few different answers and reasons, which we then iterated on and built into a really simple model centered on conversion rate. So for us, it was about building the relationship by being good to work with — simple advice, but sometimes neglected. Sending an agenda in advance, doing your prep, showing up on time, ending on time, making sure what you say has their interests in mind and isn't purely to your own gain. All of these things gave us the space to ask those other questions. 00:16:32 Pim Roelofsen: So thinking about the pain you uncovered — while positioning value you'd delivered successfully for other customers, even if slightly removed from their world — did you uncover pain they were already actively trying to solve? Or was this completely spun up from your engagement with them? 00:16:52 Jake Jeffries: What we did really well was make the metric — improving conversion rate — the center of the project. And that's a larger initiative for any e-commerce business, because frankly, that is what e-commerce businesses do. It's a business-as-usual, high-priority function at any given time. Any business case anchored to improving conversion rate is also going to help. So for us, having that become the central metric anchored the whole thing. If your conversion rate is down, you lose money every single day — and that created a lot of urgency around the project. That shift in focus — making the data-driven improvement of conversion rate the core initiative — meant every use case we built became a more powerful way for us to be one partner helping them solve a whole host of challenges, all of which would contribute to improving their conversion rate in measurable ways. 00:17:55 Pim Roelofsen: So how did you go about that, not having a big foothold in this specific segment yet, and not necessarily having a comparable reference story? 00:18:01 Jake Jeffries: It was really about earning their trust. And it was a pretty painstaking review process to bring on board one individual from the marketing team who did not report to our champion but was in a different department we needed to bring along. The group marketing director was a kind of secondary champion — but this person who reported to them was a huge blocker. She'd call us at 8pm, send me these long texts along the lines of "Hey Jake, this isn't working, I am pulling the plug" — while not actually being the person who could do that. So you get into this really challenging scenario where you need to make sure the technical requirements are covered, but not lose sight of the business opportunity. And because we were working with a real champion, because we had a strong business case around the business impact we could have, all of the technical blockers got filtered through one question: is this business-critical enough to stop us from achieving our mission? Yes or no? If yes — do we have a workaround, a solution, or are we going to escalate? In almost every one of those that came up, we were able to show that we had a workaround or a solution, and it wasn't going to stop us from reaching that ultimate impact objective. Which made the whole process a lot easier. 00:19:33 Pim Roelofsen: So at what point in the cycle did the decision criteria really start to become clearer — and to your point about influence, through the relationship you'd built with your champion? 00:19:40 Jake Jeffries: The perfect storm of MEDDICC for me is when you can actually influence the decision criteria — when you can take what a customer cares about and shape the way you deliver your solution to fit it, even more than just having the decision criteria they need. In this case, we worked backwards from their need to have a multiple-influencer, multiple-platform strategy. That was the unique element we found by really digging into online retailers. Their specific problem was setting up and managing links, and measuring success across web and app in a world where huge amounts of marketing spend was going into influencers and multiple platforms. They didn't really know how those dollars were being spent. It was hugely complicated, and they weren't seeing the return. When it comes to marketing, you want to track everything you spend. So for us, we had a solution that let them link everything appropriately, collect all the tracking data, and optimize conversion rate. All of those systems came together in a way that that became the unique decision criteria. Any solution that couldn't bring that influencer strategy to heel from a linking and measurement perspective wasn't enough to be considered in this category. And the business case showed we could directly impact somewhere in the range of £100 to £200 million in revenue on a monthly basis. 00:21:07 Pim Roelofsen: So if you talk about getting deeper and wider — that's all in that journey. Now, the economic buyer — how did that work in this deal? 00:21:14 Jake Jeffries: That was challenging. It's a family-owned business, and the CEO and CFO had a policy that they didn't really meet with outside vendors. That would have been enormously difficult to get around. So we had to get a little bit creative. What was helpful is that as we got wider in the account, our champion introduced us to his two peers — the group finance director and the group marketing director. So we had finance, marketing, and e-commerce: the three main departments who interact with our solution, plus the finance team to back the ROI. Those came together to help us build a business case based on the impact we could have. Our champion was coaching us very deeply on what the family were going to care about, the metrics they'd want to see. We ran a small test pilot to make sure it worked, showed that it was lightweight to implement, and they gave us everything we needed to put together an excellent overview business case. 00:22:35 Jake Jeffries: And then there's a funny story. When I went to go present to the group finance director and the e-commerce director — maybe five months into the UK side of things — I was running across the road to the meeting, running late, and I looked the wrong way. Cars drive on the right in some places, and I wasn't thinking. It came from the other direction — and I got hit. Luckily it was a bicycle. My headphones got knocked clean off my head, still have a big scratch on them to this day. I showed up to the meeting and I must have been mildly concussed — one of the engineers on the project said afterwards that Andrew had mentioned he saw me that day and I was acting a bit strange. I didn't really think about it until later. In hindsight, that was actually quite a monumental moment in this deal — I was potentially going off the rails, concussed. But it worked out. They didn't turn us down. 00:23:36 Pim Roelofsen: Battle scars, Jake! No one ever mentioned it! So you've shared a lot about the stakeholders, and what I like is you're constantly speaking in terms of "we did this" and "we did that" — because bringing a deal like this home is really a team sport. On your side of the engagement, what did the multithreading look like? 00:23:55 Jake Jeffries: A couple of key lines. First, our CMO was in town, and one thing I'd say to any sales rep: take advantage of those opportunities. Don't hide when your leaders are around and asking for meetings, because not everyone raises their hands. And if you have good or interesting meetings lined up, you'd be surprised what you get — a well-run CMO conversation is a real unlock. Because our CMO was in town, we got them to come down to the London office specifically to meet him. We got a little tour of their operation, heard a lot of interesting insight about the board and their challenges. There was always this kind of release valve happening above me that I could use as a really effective channel. The other critical line was making sure our solutions engineer had a really clear line to the technical team. There was a challenging technical blocker, and an implementation team, a mobile apps team, an engineering team — all these different forces needed to work with each other. Our SE, a guy called Oleg — amazing, now I believe he runs a team at Branch — he built a solution to their specific decision criteria. Knowing it or not, we now understand we built something that became a unique decision criteria for Branch. And that led us to go out and find other companies who cared about using this tool that Oleg had built. It ended up being replicated across the rest of the company and led to deals being closed around the world — off the back of this little strategy that Yusuf, Oleg, Andy and I came up with together. The technical line and the executive line were the two really important multithreading elements. 00:26:05 Pim Roelofsen: Love that story with Oleg. And would you say he was a secondary champion on your side — because this kind of thing comes up in this show a lot: the best deals sometimes have a dramatic turn where you're suddenly asking, are we out, or are we still progressing? 00:26:24 Jake Jeffries: Yeah, absolutely. What having an SE like that did was make it very clear that if the team was going to walk away from us, they would have to choose to do something completely different. They weren't going to try to build what we'd built, and they weren't going to work with another vendor, because the technical criteria of what our solution offered was unique and it specifically solved for their problem. Having someone like Oleg managing that aspect of the conversation was really successful — it gave them everything they needed to feel comfortable recommending us, and it made the commercial side a lot easier, because we could point to it and say: the business impact is real, and is only dependent on achieving the same technical criteria we've already proven are achievable. We can't separate those two things, even when the customer tries to during end-of-cycle negotiation. So for us, it helped us stick to the value of the deal. 00:27:42 Jake Jeffries: And this deal happened — as I said — at the end of 2019, running into early 2020. So we got the call that a lot of reps did, around the 14th of March: COVID is shutting down our business, we don't know what we're going to do, your deal is definitely off. Our close date was the 31st of March — end of Q1 for me. 00:28:19 Pim Roelofsen: You got that actual message in this very sales cycle? 00:28:22 Jake Jeffries: Yes — in this very sales cycle, in March 2020, this deal was supposed to close on the 31st. We had done everything. The EB meeting was already scheduled — they'd given us a kind of pre-thumbs-up. Contracts were ready and red-lined. We had literally done everything. And then the last-minute curveball was the world shutting down. When it happened we got the call: we don't think we can do the deal anymore. I was distraught. But at the same time it was a weird moment because nobody knew what was going to happen — and this wasn't the only deal I got that call on. What we were fortunate about is that this company pivoted pretty quickly, from outdoor and going-out products to — essentially — loungewear and homewear, and they did amazingly well. So literally two or three weeks into lockdown, they called me back and said: we're back on. Can we do the implementation virtually? Can we sign this? How do we make this happen? Because our business case was so strong — they still had traffic to convert — we found a way to make the pain so compelling that even a scary market headwind for a lot of companies became a tailwind for them and pushed the deal through. It was a really scary part of the deal that ultimately wasn't as big a deal as it felt, because it worked out. And it turned out to be that landmark deal I mentioned earlier — and was really instrumental in me going on to close two or three more customers like it over the next six months, in much the same deal cycle, much faster, using the tools we'd already built. That became my sign-off as I left that organization. A really nice case study of how to call your shot, influence decision criteria, connect with a champion, get to the economic buyer, and close significant deals over and over again. 00:30:23 Pim Roelofsen: What a story. A few curveballs there! So to summarize: personalization and prep led to landing the meeting in the first place. Learning about sales velocity and understanding your ideal prospect better — focusing not just on the right things in the right deals, but on the right accounts to begin with. Utilizing the wider team to get deeper and wider into the account, building secondary champions like Oleg, and building resilience into your stakeholder map. And that last point you made — headwinds becoming tailwinds — is a really interesting one from a mindset perspective too. Is there one final thing you really took away from this whole engagement? 00:31:41 Jake Jeffries: The thing that made a difference is that I had a point of view, and I was open-minded to going out and finding out whether or not it was truly correct for my customer. All those words — implicating the pain, the decision criteria, the champion, the economic buyer — are only important if you are genuinely in a search for the truth, to find out whether or not your customer is going to benefit from engaging with you. And if you can genuinely get to that truth, you have all the power in the world to ask for more, to sell to your customer on their success metrics, and it makes all the other MEDDICC stuff a lot easier. 00:32:09 Pim Roelofsen: That's the mindset thing we talk about with customers — especially on kickoffs. Is the question "is there a deal for me here?" or is it "do we truly know whether we can deliver value? If we're not sure, let's find out." 00:32:27 Jake Jeffries: Exactly. That's how this whole thing started — thinking about which customers we could provide the most value to, relative to our own sales velocity. Online retailers and quick service restaurants became two of the top segments for Branch as a result of the value that could be provided there, using a slightly different approach but more or less a repeatable and scalable sales process — all led by that initial search for truth around where our best sales velocity was. That's my really basic advice: go out and dig into the data. Have some fun with it. It's actually more enjoyable to call your shot and work deals where you feel confident, rather than searching for whether or not you can get something across the line. 00:33:32 Pim Roelofsen: So what advice would you give your ten-years-younger self if you could right now? 00:33:38 Jake Jeffries: If I could give myself sales career advice, I'd say: focus on finding a company where you can have a really lasting impact — one with good product-market fit and a good growth trajectory, and specifically a company that's going to invest in your training and help you improve your skills. The other piece of advice I would give myself is don't take it too seriously. There's always another corner to turn. It is a little bit less of a big deal than you think it is at the time — when you're ten years younger, that's for sure. And I think by slowing down a little, I've actually learned so much faster over the last couple of years — using MEDDICC as a common language, identifying opportunities for my own development, and just going out and owning them. Makes it so much more fun too. So just go and do that. 00:34:21 Pim Roelofsen: Awesome. Thank you, Jake. You've been just awesome on this. Thanks for taking the time and sharing all those valuable insights with us today. And that concludes another episode of Elite Dealers. Look forward to the next one — but for now, see you soon.
