Ryan Milligan explains Sales Leadership

Ryan, every great sales leader eventually has to become part detective, figuring out when and why the process is breaking down before the numbers show it. Given your experience leading quota carrying teams through scale, I'd love to start with this question. What are the early signals that you look for that a sales process is starting to break down?

Yeah, it's a great question. I think there are a couple ones that I tend to think a lot about. I think the first is I listen to a lot of calls and I think it's really important for a modern sales leader to be listening to a lot of calls. And on those calls, if you're starting to see a major divergence in how people are talking about the value of the product, the value of the solution you're offering and how you can be a long term partner, you realize that the training and the enablement you've done for the team isn't really sticking if people are going pretty dramatically off of a core like set of guiding principles. And so that's one thing I tend to spend a lot of time thinking about. I think the other is I often ask for qualitative feedback from people buying quotapath. I think it's really important to interview prospects and just ask, hey, how are things going? Love working with your team. It's clear that something's changing and not for the better. And then those will lead into some of the quantitative stuff. In terms of key places in which the sales process is breaking, what I care a lot about is driving urgency in sales processes. I think that you have the gift of having somebody who's interested in your product. The worst thing you can do is make them wait for next steps. And so I see spend a lot of my time and energy focused on how do we make sure I'm constantly delivering ongoing value to the buyer and capitalizing off of the urgency they presented in the process.

Sales organizations have evolved dramatically over the past decade from the heavy SDR AE handoff model of the 2010s to a more product led data driven approach today. If you were starting from a blank slate right now in a post AI world, how would you rebuild that machine?

I think the fundamental tenet is to make it easy for someone to buy your product. And that's what we've tried to do here at quotapath. So transparent pricing on your websites, they get a ballpark of how much they're going to spend, an ability to book a demo directly with a rep and not go through a qualification call where they answer questions in an email and answer questions at the BDR and then answer the same questions to an ae. An ability to trial your product for free in a product by motion. These are the kind of things that feel like the modern way that people want to buy software. You know, you hear all the time that 80 to 90% of purchasing decisions have happened before that first demo, where they've gone through reviews, understood your site. And so modern software selling is about speed and making sure that the buyer is able to accurately research, evaluate and buy your product in as short a time as possible. And that feels like the modern way to sell software. And so that's where we've been spending a lot of our time and energy as a team here at quarterpass.

There's a lot of noise around how AI might transform sales, but there's less clarity on what's actually happening today. You're close to both the technology and the go to market side. So I'm curious about your near term view. How do you see AI changing the daily workflow of AES and Revenue Operations teams over the next 12 months?

Yeah, so this is something I'm really passionate about. I think the fundamental principle is that AI is great, I think, at doing things that humans are not uniquely positioned to do. So updating next steps on opportunities, answering security questionnaires, you know, filling in fields in CRM, drafting an email. Right. Things that humans are not uniquely skilled at doing are great for AI. And that's where we've injected AI in our own go to market process. And the goal ultimately is to surge and grow the percentage of time a seller is spent doing selling activities.

You know, selling.

State of sales reports say that the average seller is spending 20 to 25% of her time doing actually selling activities. That's absurd to me. Right? You want them to be doing, you know, 75, 80, 85% of their time spent on selling activities. And AI becomes a really good tool to have specific projects or tasks that a human is not uniquely positioned to do. Have the AI do it for them. And that's how we've tried to approach the problem. I think it's a bit naive to say that AI is going to replace humans or replace sellers because ultimately what we're seeing is in an AI native world, people crave human connection even more than ever. They crave in person events, they crave being around other people. What they want is the person to validate what they're thinking and creatively answer questions for the buyer. And then what we want as a team is AI supporting the team member to give them more Time to do what they're really great at.

While most teams are experimenting with AI in small ways, call summaries, email drafting, lead scoring, few seem to be getting real competitive advantage from it. You've probably seen what's working under the hood. What's one thing I can already do in sales today that most sales leaders are underutilizing?

I'm going to go to the concept of updating CRM and moving ops through pipeline. I think it's, you know, you have the call recorders who are listening to your calls all the time. I think people aren't taking that next step to have AI gather that information and document it in a way that's easily interpretable by a sales leader. And that's what I've been spending a lot of my time with my team focused on. So it's having AI with specific prompts in our product or in our CRM. Excuse me asking the types of questions that a rep needs to answer for a customer to be a great fit for quotapath. Right. What is the comp plan that they have? What are the types of commissionable employees they're working with? Where does the data live? That's all stuff that AI is doing for my reps today so that they're actively listening on the call, not furiously jotting notes and pushing ops to the next stage in the process so that I have a really clear understanding and my sales engineering team has a good understanding of where that customer is going to be a great fit and where they might be challenged and become a customer for us in the long sales.

Compensation is supposed to drive behavior, yet so many plans either overcomplicate things or fail to align with what actually moves revenue. You've seen both sides of that equation, designing and executing. Why do so many comp plans fail to actually motivate reps? And if you had to create the perfect quote quota formula, what two to three metrics would it balance?

So I think the reason that comp plans fail the average team is because they're too complicated. And they're built as a system of protecting the cash of the business more so than as a lever to drive the right performance. Right. I think people have forgotten in the designing of comp plans that the reason you have a comp plan is to drive a human to do something that's best for your business. So the best complaints to me have a base quota structure and then a couple accelerators, especially for like a new business team on revenue based on the type of revenue that's best for your business. So let's say you want to move into the mid market from SMB. You want a comp plan that rewards your BDRs for sourcing mid market pipeline, your AES for closing mid market pipeline, your aims for renewing and expanding mid market pipeline. So you're all aligned as to what the business cares about and you've translated that into the comp plan for everybody who's involved. Really the goal is the comp plan should be so simple that I can say hey, I earn 10% on an average deal that I close and I earn the highest rate, maybe that's 16% if I close a two year multi product deal. And the reason that is is because the org cares about gross revenue retention and cares about the adoption of this new product. That should be the sentence of the comp plan. And so picking two things, one to two things, kind of like pizza toppings that accelerate the commission rate based on the parameters of the deal to show the rep. This is what great looks like. This is what the management team is going to be high fiving if you bring on board and points them to use the comp plan to drive incremental performance from the team.

One of the biggest structural decisions in a growing organization is when to specialize the AE function. Move too soon, you create silos. Too late, you lose efficiency. You've likely made that call before. When is the right moment to split AE roles into SMB, mid market and enterprise?

I think you need to find the point at which your selling process needs to be fundamentally different between those types of types of buyers. Right? If they're all going through a pretty similar buying motion for you from SMB to mid market to enterprise and one person is not changing how they're operating too dramatically between calls within SMB and enterprise customer, then keep them all within one function to keep them motivated and moving efficiently. The point and I tend to like to wait to silo candidly. And the point at which you silo is when you're at the point in which the buying process is so different that there's going to be a switching cost for the seller to transition from get off an SMB call and get onto an enterprise call at that point that tells you okay, now it's time to have more of an SMB focused rep who can fill her whole calendar with SMB types of demos and then an enterprise enterprise rep who can fill her whole calendar with enterprise demos as well. So I tend to like to wait and I like to wait until it's clear that you can have two distinct roles. You have enough capacity and volume for those two roles and that the selling motion is different enough that there's high switching costs if you're going from one.

Operational excellence gets thrown around a lot, but it means very different things depending on a team size. What's world class at 10 reps can break at 100 and vice versa. What does operational excellence actually look like at ten reps versus a hundred reps?

So the smaller your team is. So for, for 10 reps, for example, your goal is to create a sales process that is the most buyer centric and can speed them through the process as fast, as fast as possible. And that is taking down a lot of the barriers that you see in like enterprise sales motions to get them to the answer they want as quickly as possible. You are looking to replicate that, right? And those are the things we were talking about in terms of free demos, free trials, getting onto a call quickly, free, you know, publicly available pricing, what have you. The thing that changes in that like 100 rep motion is how much of this you're going to standardize across the team in terms of talk track, demo design and like exclusion criteria and gating to decide whether a person is a right fit to talk to your team. The only reason you're injecting those breakpoints to say hey, now you do have to talk to a BDR before you talk to an AE is if you find it both beneficial for the buyer to basically select out of your process potentially and for you to say hey, these are the only types of customers that this rep needs to talk to because they're so high value, they should go to my most high value rep. So in principle, the way that I think about it is you're building the same fundamental structure you're building at 10 versus 100 reps which is buyer centric speed to purchase and making it easy to purchase and research before they come to you. What you're adding when you get to 50 or 100 reps is those hurdle points along the way that allow both you and the buyer to figure out if you're in or out and what the happy path is for both parties.

Revops revenue operations has been a hot topic over the past couple years. I think it's something that many people see as a very strategic role. But how do modern RevOps teams actually act strategic versus being perceived as strategic?

Yeah, it's a really good question. I think a lot of the question I get a lot is RevOps leaders want to be more strategic and less CRM. Admin and how do they do it? Right. And I think the thing that I always say is what you're trying to do is look within your organization to identify problems and proactively come up with solutions to those problems. Right. So the Rev Ops team that is the ticket taking, hey, can you change this field in CRM that's a hard gap to be strategic because you're, you're getting asks from other people in the organization. But the rev Ops team that's saying, hey, it looks like our qualified rate of demo occurred opportunities isn't where we want it to be. I watched a couple of calls. Here are some snags we have in the process. Could we design a new way of better qualifying these customers, for example? That is somebody proactively seeing a problem within the business, leaning in and proposing a solution to that problem. And that is way more fruitful for the strategic nature of RevOps than being, you know, reactively asked questions or asked to do things. There are other things in a business that don't tend to actually be someone's job title like pricing and packaging changes, contract design changes, comp plan design. All sorts of things that RevOps can proactively step into and go to a CEO or go to a CRO and say, hey, this feels like a snag in our process or this feels like a challenge. Could I captain that cross functionally within the organization? And I think the more RevOps teams are spinning up those internal tiger teams to solve those problems, the more they're seen as strategic to CRO CEO.

There has classically been tension between sales teams and marketing teams and sometimes they report to different people, but you have both of those teams reporting to you. So you have this centralized view of marketing and sales. What efficiencies has that led to?

Yeah, I mean the classic challenge is marketing throwing the leads over the fence, complaining that sales isn't following up with them, and then sales complaining that the leads weren't very good. Right. In centralizing kind of a go to market function here. Quotapath. So marketing, sales and revenue operations, what we've been able to do is get everybody aligned to the fact that our unit of measure is new revenue. And so marketing acts in service of driving our ability to grow our new revenue from new customers. And so what that means in practice is marketing's running webinars, but then writing copy for the reps to use to engage disengaged opportunities to invite them to webinars to get them back on the hook. Marketing's running dinners and Having the sales team join and bring some prospects and some existing customers to those dinners to drive value and have really great conversation. And so when you have a marketing team that understands how the proverbial sausage is made down funnel and sits within that they get feedback on the quality of the leads that they're actually passing. They're able to better support the sellers in real time. And that whole go to market engine is working on driving new revenue together versus the classic attribution blame game that happens a lot of orgs that frankly is a huge waste of time.

You are a RevOps revenue operations leader and you're now leading a sales team that is unique. Why has that benefited you and do you think we're going to see more of that?

I do think that more CROs are going to come from RevOps. It's a theory that I've had for a while and I think it's because ultimately the CRO their responsibility is and their peer level is to their management team and what they're responsible for is driving profitable, efficient, sustainable growth. Right. They when you have a rev Ops leader come in to lead a sales team, a couple of things happen. One is they're prioritizing their work and I'm prioritizing my work and my team's work based on what I believe is best for the business writ large, not just based on what's best for for new business. And that allows you to bring on better fit customers who have longer term growth potential within the business then chasing down that last deal that might not be a great fit at the end of the quarter. I also think you have a really nice balance between a sales team who's grown up through the sales org who knows a lot about the art of selling and can do that really well, paired with somebody from a rev Ops capacity who can bring more of the quantitative science of the sale and understand where the breakpoints are in the sales process and how they can build processes to improve that. So it's been incredibly fruitful for us. I've learned a ton as a new sales leader from the reps themselves, but it's nice to have people with two really different approaches and backgrounds working together between rev Ops leader running a sales team and sellers on the team to push each other and build a collectively more efficient and better operation. Cool, that's great.