Hello Dylan, Sonia, and thanks for inviting me. I’ve been really fortunate in my career. I’ve had great roles, both in large software companies, and small startups, from EzGov to HP, and from Dun & Bradstreet to UiPath. I have always been in growth roles, where a new business or a business unit needed to be created and scaled, enterprise-facing, typically dealing with complex sales processes, both B2B software and B2B solutions. At EDS, HP’s US Government division we did billion-dollar outsourcing deals, and at UiPath and EzGov, my focus was to build a relatively new sales motion, in a more business-oriented vs. IT-oriented motion.

In my first sales role at DocuCorp International, in the late 90s, I was a one-man team looking after about a dozen immediate customers from Atlanta. In my most recent role with UiPath, where I was the first go-to-market employee in the US, I helped build the Americas business. To me, that was a great hyper-growth experience in a super hot market, with a company that got the culture perfectly right and where we had a lot of lessons learned through every step of the journey.

Since leaving UiPath in 2021, I’ve enjoyed a bit of downtime, seen my daughter off to college, and focused on assisting startups that are ready and want to go big.

The first critical thing that comes to my mind, and it is not only US-specific, but an important milestone for any territory that you’d expand your business into, is choosing the right type of leader. From my point of view, this professional needs to be a versatile leader who can go from strategic to tactical on a dime. In the early days, there are so many things to figure out that are either sales motion-oriented or sales machine-oriented. They change all the time, and it really falls on the first GTM hire to drive that.

This leadership is critical, but there are other things equally important, like executive involvement. As a founder, you can’t just hire a country manager or GTM head, hand them a market and expect them to deliver. Geographic expansion requires heavy C-level involvement, and a market like the US is important enough to potential require relocation.

Then, you must think through the full GTM cycle. What do you want to have in the US and what do you need to have? The first step is direct and indirect sales, but you need to consider having localized customer success, professional services if that’s applicable, or sales engineering. Then, what is your strategy to generate leads? Where does marketing fit in, all the way from the marketing lead generation to the value delivery for customers? What it will require for you to make investments in, to make that first nucleus successful? On top of it, you have the corporate services that are needed, like HR, finance, and legal to ensure the local team functions properly.

A common mistake I see companies make is underestimating the challenges of selling their product in a new region when they have less brand awareness on the ground. In these situations, founders often overestimate how successful a salesperson can actually be, without all of the other important supporting pieces around them.

When I started at UiPath, I had to go find the location and the space for our office. This is an example of a very tactical task. But I also had to build the 2017 GTM plan and structure the sales team so that we’d be able to reach our sales target. In those first few quarters, that’s how the days are. You’ve got to be able to be in a deal, jump in a call with a customer, while also being able to take a step back and say “I’ve done four or five deals, we’ve tried to sell to the CIO, and we got consistent feedback, but it’s not working. So we should consider not going after the CIO, let’s consider the CFO,” for instance. That ability to step back, reevaluate, and adjust on the fly – that is what I find some sales leaders don’t have the capacity to do, because they’re constantly just going from deal to the next. If you can’t step back and think purposefully about your strategy, then you can’t make conscious decisions and you’ll lose time, which means you won’t grow fast enough.

There are two challenges the first salesperson on the ground faces. First is establishing the sales motion, which can be defined as a set of repeatable steps that lead to predictable sales success. This is a big task, defining how to sell a product.

The second challenge is to design, implement, and grow the go-to-market machine that exploits that sales motion.

When you start a new company that’s defining a new market you don’t have either one. There is no playbook, and there is no GTM team – yet. Just because you have a good product, does not mean you have a sales motion. The experience of building a sales motion is not something that every successful sales leader has had. If you’re a sales leader who has only ever worked in a big company, you may have never had to build a sales motion from scratch. Either you need to have been in a startup or been in a new division to experience that.

A sales motion or a playbook requires a lot of fine-tuning and conscious learning. You need to think about it and do lots of experiments to get it right. For example, will you pursue a freemium model? Are you going after a particular persona? A particular buyer? When you start out, you don’t know the answer to that, but you got to go out and try it, observe it, learn from it, and this really puts quite an onus on the type of sales leader that a startup would need.

Your first sales hire needs to have done that before. They need to show a lot of versatility and for this, the profile I would suggest is in the middle: A sales leader with strategic and tactical experience who has successfully managed those two sets of tasks – playbook creation and team establishment – and has the ability to grow with the organization as it grows. Someone who will act initially as a player, and then as a coach for the rest of the team.

If it’s a technical founder or product-oriented founder, then crafting the sales playbook may be challenging for them. Part of the reason why is that the more elements you can have in a playbook, the more comprehensive it is, the better it is. Early deals provide lessons that can be fed into the playbook, which is valuable. In my view, at the end of the day it is the sales leader that owns the sales motion, especially when it’s a new market. But whatever a founder can give them initially to get started is important.

Now, as to what makes an effective sales playbook – there are a lot of industry consultants and sales technology companies out there who sell services to help companies build a sales playbook. But in my mind, and this is debatable, an effective sales motion is about repeatability and about having a lot of established and agreed components for a sales representative to apply to every opportunity. In the end, this leads to more predictability in how reps should behave in a given scenario with a prospect, which leads to more predictable outcomes.

There should be clear qualification criteria for leads and opportunities, differentiated by different types of buyers, and what it takes a lead to become a “qualified” lead. There should be measurable sets of steps to go from lead to close, and what a good demo or presentation deck look like, and how to do a good proof of concept.

In addition, as the sales motion is designed, it should engage the prospective customer as early as possible, providing access to things like free trials, customer references, and other assets that really promote self-service from the customer’s perspective. There needs to also be a strong sales technology stack, and a strong feedback loop for the sales representatives. Reps should be getting as much information and feedback as possible.

Lastly, to me, although it may sound derogatory, it’s not intended this way, but the fewer decisions a sales rep has to make, the better it is. The more the sales motion can be prescribed, then the more the sales rep can be with the customer, engaging, convincing the customer, and closing the deal.

One aspect that worked well was hiring versatile leaders. All the people I hired early on were people who were willing to dig in, roll up their sleeves, and get out of their comfort zone, who could chase deals, learn, and build a team to lead. Many of them had amazing careers at UiPath, and some of them are even still there.

The other aspect I think we got right was developing a sales channel from the beginning. The second person I hired, Arjun Ayer, was all about figuring out how the channel is going to help us. We knew there were multiple ways for that to happen, either working with partners as a seller or a sell-through, or as customers. Just charting out who might be our early adopters, was pretty big. I remember on Christmas Eve, in the first year at UiPath, we ended up doubling our business in the US, which had a big impact on our Series B that happened three months later.

We were very good at going after the big logos. We were focused on landing Exxon, we snatched Walmart from a competitor. The initial revenue wasn’t big. They were pilots, but they generated good early references. Momentum built that led to traction in the market, which paid off fantastically well in the long run.

You can’t rely on the vendor partner machine that the systems integrators and consultants have. Because to your point, they will swallow you. For UiPath, a solution was to find individuals in these big organizations who care about what you’re selling for the precise reason that they have customers whose needs align to the value you provide. At UiPath, Gabriel Pana did a great job building that relationship with EY in Houston. They had customers in the oil and gas businesses who had issues, and we could help solve them. This is how the collaboration started, from solving that nucleus of issues, and then extending to other customers in different verticals.

Then we focused our strategy on a few such partners, as you can’t really have a quality relationship with thousands of them. Soon after, we decided that this is a really good potential accelerator for the business. So we started hiring partner-level people from the systems integrators. They know their organizations extremely well. They’ve worked within them and know how they function, and can help manage the relationship much more effectively.

In the early years as a company you tend to be more interested in customers than revenue. When in land-grab mode, you want to get as many logos as possible and one of the tools you should have in your bag is the willingness to discount, especially if you’re in a competitive space. For the large logos, you may simply have the opportunity to get a departmental sale, and then can claim it as a logo. You can potentially secure them as a reference for that particular industry. If the GTM team is structured where the rep owns the account, then he or she will have plenty of opportunities to up-sell over time. ***In the customer journey/sales motion you create, how you scale from deal one to deal four takes a real part besides the renewal.

Companies need to be careful in striking a balance between the acquisition of big logos and the demands they have in terms of feature customization. It can be distracting for the product team, and to your point, the features may not be relevant to other customers.

It’s a great interplay between the customers, the product team, and the sales team. Early on there should be a lot more willingness to accommodate a particular customer’s feature requests. Over time, that process should become much more strict and more oriented around product releases and feature release dates. That said, it is important to maintain focus on a list of target accounts, i.e. strategic accounts before they were formally “strategic”, where as a company you are willing to go the extra mile in accommodating them.

For example at UiPath, we knew that for some customers, we were going to do professional services. So we decided early on to make that happen and actually run our own professional services track for certain strategic customers. We knew we could trust them, and we needed to know how our product actually stood up in a services track. From that experience, we learned a million lessons.

Over time, that process needs to tighten, because companies will have too many reps and too many customers to accommodate the various services and change requests, and you want to stay focused.

To me, the hiring process is one of the things that the first sales leader has to really learn how to do well. But it is a constant evolution. In a startup, attributes like versatility, resourcefulness, and cultural fit tend to really outweigh big company experience. These are factors that increase a candidate’s chance to succeed in the business.

In interviews, I look for multiple things, but how a candidate engages with me in an interview is critical. That first conversation gives you a hint of how they may treat a customer or a colleague, if they are respectful, if they really listen, and ask thoughtful questions.

I try to ask unexpected questions. One of my go-to questions was “How do you learn?” This gives you an insight into whether people are consciously learning or not, whether they can think on their feet, it’s amazing, the spectrum of answers you get to that question. Then, I tend to look for specific situations from their experience which show what they did to demonstrate a certain important attribute like tenacity, when have they been tenacious, when they rescued a deal, and what was their contribution.

Lastly, a constant evaluation process is key to learning and improving your team and sales playbook. We frequently analyzed the backgrounds of our successful reps, what were some of the attributes that they actually brought to the business. Our best reps were business sellers who had large and small company experience.

In a sales leader you look for the ability to coach, mentor, and evaluate, which comes with a high level of EQ, the scope to get the best out of their team, and of course strategic thinking. They need to be able to manage the complexity of the role, which brings a lot of number crunching, and a lot of forecasting. A sales leader needs to be willing to go solve a sales deal issue that a rep can’t solve. They also need to communicate well as they will communicate on behalf of the company.

Something I believe in, and this can be a bit controversial, is that a sales leader’s team is the team that they report to, not their reps. What I mean by that, is that when big things happen in the business and a decision is made such as an acquisition or pivot, which impacts the individual rep, the behavior you want from a sales leader is first to buy into the decision and then execute what is in the best interest of the business. That may not always be the same thing that is in the interest of the rep. Obviously, they should advocate for the rep and be their coach, mentor, and supporter, as I said before. But in the end, the decision whatever it may be, the sales leader still needs to execute for the business.

I would say that between a sales leader and a founder there needs to be a tremendous amount of trust and respect. Being complementary to each other is a key aspect, otherwise, I’ve seen lots of examples where it makes things more difficult. It is a relationship you’ve got to constantly work on it, and frequent communication is the basis. A founder speaks for the business, so helping solve issues on a regular basis and being available to assist the sales leader is important. A sales leader brings a lot of GTM experience that not every founder has and helps understand how the market works and helps the company.

At UiPath for me was easy, Daniel Dines was the main reason I joined the company. I always trusted his vision and the type of company he sought to build. But I also knew that what I brought to the table was complementary to his skillset, and I was confident that I could really help him.

There are multiple ways of doing that, but the first step would be to decide if you want industry teams or geographic teams.

At UiPath we ended up with a hybrid structure because of finance/banking and government, two industries that tend to be repeatable with a unique industry-specific sales motion. It can be an efficient way of organizing a team because there are a lot of banks and government agencies to sell to, for example.

Aside from those two verticals, at UiPath at that time, we best obtained coverage through a geographic model. If you think of the market pyramid, we always focused on the top part of the market, on the largest customers, the enterprise customers, which is massive. There are thousands of enterprises in that segment.

It all comes down to focus. You should focus your reps as much as possible, so you should help them qualify the leads very well.

A second criteria would be deciding how big the territory should be. Initially, we started out with 100 customers, which is an insane number. It eventually came down to 50, and then 25 within probably a year.

In terms of targets and revenue quotas, within the segment, it all boils down to a bottom-up model consisting of the average contract value, the number of deals which can be done, and correctly measuring the length of the sales cycle. Across segments, strategic accounts deals tend to be bigger within enterprise segments.

For a sales organization, culture is a big potential differentiator against the competition. Customers feel how you treat them. They see how team members interact with each other and collaborate. If they respect each other, especially in B2B, where you expect customers to have a long-term relationship with you. I’m a big believer in culture as a differentiator and ultimately if you think about it, sales is a team sport, right?

The big question is how do you foster that in a distributed team?

First off, the right leadership style is a big factor in fostering a healthy and effective culture. Being the role model for the right behavior, and promoting and rewarding it, while correcting improper behavior without hesitation.

Another key part is over-communication, not just on matters of sales, but having lots of town halls and meetups together if possible. One-on-one coaching should be available for every new hire. In my view, the sales leader actually owns the onboarding process and is responsible for its success.

Avoiding toxic culture starts with hiring, where you are not only looking at the hard skills and experience of the individual but at the team and ensuring there is a cultural fit as well.

My pleasure. And to the founders out there thinking about geographic expansion, be willing to go! Build a thoughtful strategy, get the right leader in place, do it as early as possible, and go big!