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HOUSEKEEPING 📨

Pretty excited to share today’s piece with you. This is the second of our new post style, where we learn from experts in their field. The first was with compensation guru, Matt McFarlane, and today, we are hearing from Scott Leese. Scott has a crazy background, being involved in some way with 12 unicorns and 11 exits. You’re going to love it.

How’s everything else going?—well, pretty good I think. Athyna’s web traffic is up 500% since we launch our creator program, and growth in our pipeline is strong. I am going to write about our creator program soon. It’s really interesting stuff. And the newsletter is going great. It’s a lot of work doing this while being a founder & CEO but I really love it. Thanks for being here and reading it.

EXPERT OF THE WEEK 🎙

Scott Leese, Fractional CRO & GTM Advisor

Scott Leese is one of the leading startup sales experts in the U.S., based in Austin, Texas. He’s the CEO and founder of Scott Leese Consulting and Surf & Sales and has been a strategic advisor to over 130 companies worldwide.

With nearly two decades of experience, Scott has led multiple sales teams to success, worked with 12 unicorns, and been part of 11 exits. Known for building scalable and successful sales strategies, he’s also an Amazon best-selling author and a sought-after consultant and trainer, making a lasting impact on the startup sales landscape.

What are the most common sales strategy mistakes you see in startups today?

One common mistake is going after the largest possible customer in their ICP way before they're ready. For instance, imagine Bill and Scott just started a company, and they know someone at Adobe who could potentially bring in a $2 million deal. It seems like a game-changer, but once you get into those conversations, even if you're lucky enough to get in, it can take forever. You lose momentum, get distracted by Adobe’s requests to build features you haven’t developed yet, and you take your eye off the ball from a product standpoint. You also don’t get enough practice or repetitions to figure out if your pitch resonates or if you can move any deal from one stage to the next. If you miss, which most do on these big deals, you end up burning 6 to 18 months of runway and probably miss your chance to talk to those companies for another couple of years. It sets everyone back.

Another mistake I often see is having a completely unfocused ICP. Some startups think their company is better if they can sell to everyone, believing their TAM is massive. While that might sound great, it’s not ideal in the beginning because you need to know where to start. Conversations with a $50 million company are very different from those with a $50,000 company. If you're talking to someone with 17 people on their buying committee, it's a different process than dealing with just two people. You're asking your sales team to do too many different things at once before any of them have been proven. These are two mistakes I see regularly, and I often find myself telling people to slow down and reassess their approach.

How do you scale a sales team quickly in a high growth environment?

Hiring the right people is kind of where it all starts and ends. It’s crucial to create and develop a culture of coaching, training, and continuous development. It’s a mistake to hire really good people and then just leave them on their own. You need to coach them up and provide the right environment where they’re supported.

At the same time, you need to get everything out of your head and onto paper, creating a process that everyone can follow. You don’t want six people pitching your products in six different ways, right? You want everyone more or less following the same methodology—using the same kind of elevator pitch, handling the same objections in a consistent way, and differentiating from competitors in a way that’s clear.

When you hire the right people, coach them effectively, and establish a repeatable, well-documented process, you set the early foundation for helping your company get off to the right start.

How should companies approach enterprise and moving up market?

First of all, I would wait until you’re really confident that your SMB motion is rocking and rolling. You want it to be steady, growing, and predictable. The approach changes quite a bit when you move upmarket. For example, the way you prospect is probably different. If you’re selling to SMBs, you might be able to make 100 cold calls a day and get people on the phone. But that strategy won’t work if you’re selling to the Fortune 500. You’re going to have to be much more thoughtful, do more research, be more strategic, and network your way in better.

You’ll also need to really understand these companies’ businesses in ways you aren’t required to in an SMB motion. There will be way more people involved, so you’ll have to grasp all the different buyer personas—what the CFO cares about, what the CEO cares about, and what the frontline worker cares about, including how your solution is going to help their day-to-day jobs. You’ll also have to deal with legal and procurement, and probably do more negotiation on pricing.

Pipeline management also becomes more complex because deals don’t just pop up and cycle out quickly. They might take a long time to mature, so you need to build a strong pipeline early on and keep feeding it. To guarantee success, you should aim for a pipeline-to-target ratio as close to 12:1 as possible.

All these factors—understanding your product better, getting support from customer success, sales engineers, or solutions architects—will change your approach and sometimes even the DNA of the salesperson you need to win those kinds of accounts.

What metrics should founders and leaders be paying the closest attention to?

I think the pipeline-to-target ratio is a huge one. Startups have been fed this line from VCs and big corporates that a 3:1 ratio is what you need. But that doesn’t work in early-stage startups. In those early days, you have no idea what you’re doing. So if you want to take a big risk of missing your targets, go ahead and aim for that 3:1 ratio. But if you want to guarantee success, push everyone to get to a 12:1 ratio. I used to obsess over that pipeline-to-target ratio, and for good reason.

Nowadays, my go-to metric is network growth. It’s getting harder and harder to succeed with just cold calls or cold emails. You’ve got to take advantage of referrals and warm introductions, but you can’t run that play if you don’t have a solid digital network. So I’d be telling everyone on my team, "Hey, you need to add 10 to 15 new people a day—100 people a week." I want to see that network growing because, in theory, that gives you access to more warm introductions.

_{*Note: Check out this super cool playbook Scott features in, written by one of his portfolio companies.}

Of course, there are still the old-school metrics like average contract value, conversion rates, and sales cycle length, which depend on the environment you’re in. And I still see value in tracking how many touches lead to conversations, how many conversations lead to meetings, and how many meetings actually hold. So yeah, a couple of the old metrics, and one or two new ones—it’s all about adapting to what works.

How will personal branding impact the structure of sales over the coming years?

I actually think that if you don’t have any kind of brand and you’re not producing content in the next few years, you’re going to really struggle to succeed. What used to be seen as a distraction or a unique edge is now becoming compulsory. Building brand awareness is key, and nobody is spending money on SEO and AdWords like they used to. Now, you’ve got founders running huge brands, creating all the interest and demand through their social channels, bringing in warm leads. Salespeople have essentially become their own marketers.

If you and I were to take a job at a startup tomorrow, the visibility of that company would instantly go through the roof because we have more brand visibility than the startup itself. Suddenly, without spending a dime, the startup gets what amounts to hundreds of thousands of dollars in theoretical ad spend, just through the value and number of impressions. That’s how people get validation and find trust these days. They don’t go to static websites like G2 Crowd or Yelp anymore. They go to communities or talk to their peers, asking, "Hey, I’m looking to buy such-and-such. I’m also considering these other two competitors. Which one’s the right one?" And they trust the word of whoever they know and respect out there.

If you have a trusted brand that’s been cultivated over the years, sharing valuable information, and you say, "This product is good," or "I’m representing this thing over here," the inherent trust is already there. So, you’re through one barrier already. It’s also a great way to nurture leads. Someone might hear you on a podcast, find what you said interesting, and then follow you on LinkedIn. Over time, they engage with your content, and when they move into an executive role, they remember you. Suddenly, you get a message: "Hey Scott, been following you for the last couple of years. Love your content. I actually want to talk to you about your services. I’m kind of struggling with this and that." And just like that, you’ve got a lead. It’s not immediate, but it’s been developed and nurtured over time.

If you don’t have that mechanism as a salesperson, you’re really going to struggle in the next few years. As for how sales teams are going to look, I think we’re moving away from the SDR-AE model. Personally, I never had that model; I always had full-cycle salespeople. I think we’ll return to that. As AI continues to improve, it’ll smooth out the bugs, like imperfect content or delays in AI-generated calls. A lot of low-level tasks will just be automated away. What do I need an SDR to do research for? Or an LDR for lead enrichment? These roles are just expenses now. Everyone in the VC world is talking about the first two-person billion-dollar unicorn or hitting $10 million ARR with less than five employees, or even $100 million ARR with less than ten. Growth isn’t being discussed in the same way as it used to be.

So, it’s hard for me to imagine a future where you’ve got an SDR, an AE, a sales engineer, and all these siloed roles. I think those will eventually disappear, leaving only the best of the best AEs—people who are well-networked, who create their own demand, and who can prospect as well as close deals. I see a lot of contraction in the sales industry coming, though it’s hard to say exactly when. But it’s difficult for me to see it going in any other direction.

What else do you see changing with AI and sales?

I think there’s going to be a continued push among startups and VCs to find ways to automate the entire sales organization through AI. Sales is a massive expense—you’ve got the people management load, skill gaps, and time constraints. In theory, all of these issues go away if AI is doing all the selling. It’s hard for us to conceive because we didn’t grow up that way. But if you talk to kids who are preteens or teenagers, they don’t care about interacting with a human being to make a purchase. It’s not even something they think about.

I hear people say, "Humans will always want to buy from humans," and I say, well, that’s bullshit. My 14-year-old doesn’t care about interacting with a human to buy something. I’m 47 years old, and I barely care about it. I barely want it. I just bought an investment property a couple of months ago—$1.1 million—and I never spoke to a person on the phone. Not the realtor, not the lender, not the inspector—nothing. It was all done via email and text messages. When I tell people that, their eyes light up, and they give me this look like I’m crazy for making a million-dollar purchase without talking to a human. And I’m like, "Why? All the information I needed was at my fingertips."

I don’t think we buy the same way we used to, and that shift is going to be massive once today’s teenagers become tomorrow’s buyers, sellers, and executives. There’s a huge push from the builders of these AI tools to figure out ways to have a fully automated SDR, a fully automated sales coach, and a fully automated AE. Whether they’ll be successful or not remains to be seen, but I think it’s inevitable that we’ll go in that direction. I don’t know if we’ll be able to pull it off completely, but that’s definitely where things are headed.

How can companies create a sales culture that attracts and retains top go-to-market talent?

First and foremost, you have to sell something that works. The product has to be good; it has to solve major pain points. It can’t just be a nice-to-have little widget. If you’re aiming to build a super successful sales culture, your product needs to be something that people can’t do their work without.

You’ve got to provide opportunities and be supportive. This means offering a clear career path, investing in coaching, enablement, proper onboarding, continuing education, and helping people with their pitch. If someone wants to move from an individual contributor to leadership, you should support that. Spend time with your team, genuinely care about what’s going on in their lives. Have one-on-ones that aren’t just about pipeline reviews—ask, "How’s it going, Bill? How’s your health? How’s your family? What are you working on? What’s your goal? What are you trying to do next? Are you trying to buy a house, get a down payment?" And then, "How can I help?

In my experience, this is what creates a culture that attracts, not repels. When you do it right, recruiting becomes easy because word of mouth travels fast. People hear about it and start asking, "Is this a good place to work?" I used to have interviewees come in and ask me that, and I’d say, "I don’t know, go ask all those people on the floor." I’d let them talk to everyone, no restrictions. If I’ve done my job, my team shouldn’t say anything I’d be embarrassed about or that would turn off a good candidate. And if they do tell the truth and it scares someone off, well, maybe that person wasn’t the right fit anyway.

Transparency helps a lot, as does access to information and the right people. But at the end of the day, it’s all about genuinely giving a shit about helping your team members get where they want to go. It’s not about me hitting numbers or looking good. If I can help Bill achieve his goals, and he moves on in two years because we don’t have the right role for him, I’ve still done my job as a leader. We, as a company, will have invested in a really good employee who goes on to do something great, and that reflects well on us, not badly.

How do you identify who will be a top performer when hiring?

Honestly, if anyone had this figured out perfectly, we wouldn’t be working anymore. We’d be on a beach somewhere sipping mai tais because we’d have sold our business for a trillion dollars. Nobody has this figured out—nobody. I’ve hired and fired thousands of salespeople, just like many other leaders and so-called experts, and I’m telling you, it’s really freaking hard. Really, really hard.

For me, I don’t care much about someone’s employment history, track record, past numbers, or successes. To be honest, that stuff doesn’t matter as much to me. What I care about is who this person is across from me. Where do they want to go next? Why do they want to go there? Why are they now willing to do what they’ve previously been unwilling or unable to do? Are they open to feedback? Are they humble? Do they appreciate and respect each opportunity that’s put in front of them? Do they understand the fragility of life? Do they have a strong sense of urgency to make something happen?

These are the things I care about far more than who someone has been. I care much more about who you are now and who you want to become. I try to surround myself with as many people as possible who have that kind of vision. Like, whatever I’ve done before doesn’t matter—I’m here. I’m just looking for someone to help me get to where I want to go and teach me the ways. And I’ll run through a brick wall to make that happen. That’s what I try to optimize for.

And that's it! You can also connect with Scott on LinkedIn or explore his work at Surf & Sales to learn more about his expertise in building top-performing sales teams.

BRAIN FOOD 🧠 

Just read Anu Atluru’s take on the emerging trend of Silicon Valley small businesses, or SV-SBs. She's spotting a new kind of startup that blends the scrappiness of small businesses with Silicon Valley’s tech-savvyness.

The idea is all about growing efficiently without necessarily chasing after big venture capital. Atluru thinks this could be the next big thing in the startup world, especially with tech and marketing tools becoming more accessible. It’s a cool perspective worth checking out if you’re into startup trends.

TWEETS OF THE WEEK 🐣 

TOOLS WE USE 🛠️

Every week we highlight tools we actually use inside of our business and give them an honest review. Today we are highlighting Attio—powerful, flexible and data-driven, the exact CRM your business needs.

See the full set of tools we use inside of Athyna & Open Source CEO here.

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