On this episode of the ‪@WhatWorked‬ podcast, Tyler Rachal and Mike Wu sit down with Frank Golden, Principal at Golden Ventures, which offers GTM advisory and fractional CRO services. Are you thinking about sales at a startup? Listen to this episode to hear lessons and experiences from Frank.

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We covered a ton of great topics:

• The challenges founders face getting their first 10 customers (and $10 million in sales)
• The sales math to figure out the required pipeline and quotas without historical data
• The "death" of outbound and the birth of AI

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Transcript edited for clarity:

Tyler Rachal

Welcome everybody back to what works. Yes. Thumbs up, Frank. I am very excited to welcome a very special guest for this is now episode 11 lucky number 11, aren't they all lucky except for 13? We've got Frank Golden joining the pod today. I have some personal background, I've known Frank for a very long time. We’ve got a bunch of war stories from being early employees at fast growing startups. We've lived to tell the tale. I'm excited to have Frank on for a bunch of reasons: I think he's going to be able to shed some really great light on the current landscape for go-to-market for these fast-growing venture-backed tech companies. And also, you know, Frank is also gonna be able to give his two cents on just tech in general and starting his business, Golden Ventures. So on that note, Frank, if you don't mind giving a quick background about yourself and what you're doing today with Golden Ventures.

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Frank Golden

Totally. Thank you, Tyler. And yeah, it's great to be on with you and Mike. My background, so I was raised in New York, went to school in Boston, then moved to San Francisco and did four seed stage startups over 10 years. So I joined twice as one of the founding sales members and then twice as the sales leader. And I've seen that journey of like zero to 10 million in revenue four times. And in the last year, I went on my own, started advising business where I help startups at that phase as well either with founder coaching or fractional sales leadership.

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Tyler Rachal

Love it. And I think you're being extremely humble, Frank, in the sense that you didn't just join, you know, any startups, you want to rattle off some of the names. I feel like these are big companies now and you've also been present for a lot of companies that have been acquired and then there's going to be hopefully some future exits for the companies you were at. Who are those companies?

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Frank Golden

Happy to, so I started at Oracle, got some sales training. A lot of us jumped to startups right after that. The first startup I joined was RelateIQ. An amazing experience as my first company, I joined as the second SDR there and met amazing people I have relationships with. The second startup was a company called Talkdesk. Actually, RelateIQ was sold to Salesforce. That was the first exit. It was very quick, but I got the taste of startups and got addicted.

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Tyler Rachal

Yeah.

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Frank Golden

I went to a company called Talkdesk where I followed a buddy of mine and a partner Spencer Wiedeman to go work for a VP Brendon Cassidy to be an expert in sales, learn from the best. So I went to Talkdesk for two years, that was an amazing experience. Typical startup stuff like starting in an old dentist office to moving into like the newest high-rise  in SF and like having all the space and writing boosted boards around the office and things like that. That was fun. We went from two to 20 very quickly and a very big team selling contact center software. Then from there, I went to a company called Beyond Pricing, which was my first stint in vertical SaaS, to lead their team. And we went one to 12 very quickly there, really fun building with that team. We were selling a dynamic pricing algorithm into short -term vacation rentals. So dynamic pricing works for a ton of things. It also works for vacation rentals. Did very well, great product market fit. They're continuing to grow and have done very well. And then the last one was back with the RelateIQ team, a company called Airkit. And it was a low -code platform designed to automate customer interactions and did that for three and a half years with an amazing team that also exited the Salesforce with the same team. And that takes me to here.

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Tyler Rachal

Amazing and I remember that talk desk, swanky new office. I mean, you know, you've made it when you've got one of those elevators where there's no buttons. You just got to get in, you're at the mercy of the elevator, sticking you to your final destination.

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Frank Golden

Yep, that's it.

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Mike Wu

Frank, your experience is unique, I think, in many ways, but one of the ways that you've done the zero to 10 thing four times. For someone like me and anyone who might be listening that never had that experience, what does that feel like? What does a company that's going from zero to 10 feel like? You kind of alluded to one thing, like you started off in a dentist office and then moved to a high rise, but just what does that zero to 10 look like for anyone that's kind of on the outside of that experience?

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Frank Golden

For me it feels like the closest thing I can relate to is like team sports with the best team you've ever been a part of. So what it feels like, it feels like you're a founding member of a startup. Like you're not the founder, but like you're there and your voice is there for a reason and your opinion is there for a reason and people trust you to speak up. That's really empowering, even at a young age.

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It's extremely exciting because like if you have a product market fit, you grow fast and you raise rounds and you have a lot of milestones to celebrate. First 10 customers, A round, B round, new offices, all that stuff is super exciting. Getting to travel and meet customers in different countries and different states across the United States, getting responsibilities you would not be given otherwise at larger companies. So, I mean, don't get me wrong, they're very difficult and there's a ton of times where it's your life. But in your 20s, if that's what you want to do, it's a great path. So I have tons of amazing memories from the four startups.

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Tyler Rachal

Absolutely. And I, I also too know from just knowing you personally, you've always been a big game hunter. I feel like you were always on top of the biggest companies and I'm just kind of curious. I always love talking old sales war stories. Do you have a memory of a particularly big deal that you closed at one of those companies? That feeling of taking that moment back to the team, I feel like at a small company is always incredible. It's so different than if you were at a giant business like Salesforce.

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Frank Golden

Totally. The most recent one is at Airkit. We worked a very fast, very big deal with Morgan Stanley. 

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Tyler Rachal

Wow. Heard of them.

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Frank Golden

And it was fun for so many reasons, it was a team effort. So everyone on the team was on it. It was a lot of in-person working and flying to like their office in Menlo Park, going to purchase, going to Manhattan, meeting with hundreds of people at the end of a six month cycle. And I couldn't have enough good things to say about the Morgan Stanley team. They were incredible to work with, move mountains in order to do what we wanted to do together. And it was a landmark deal for Airkit and probably helped us to do what we needed to do to eventually exit to Salesforce because we had such amazing Fortune 500 logos for such a young company and that really was just a testament to the team executing at the highest level and having a product that could support it. 

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Tyler Rachal

That's incredible. And I think, Frank, you had some really great wording for it, but I would say you're an example of this. You mentioned that the real killers in sales, the people that are out there in go-to-market that are really doing it, they're crushing big deals, they're growing teams. You made this note to me in passing about those aren't the people that are out there on LinkedIn talking a big game. They're too busy closing deals. And I think you're an incredible example of that. I'm curious, as you decided to start Golden Ventures, as someone who's in that profile, you could easily go work for a bunch of technology companies and be a quota carrying salesperson if you wanted to, employee, et cetera. But instead you decided to start a business. For other people that are like you, that would want to do the same thing, how do you make that leap from going from employee to business owner?

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Frank Golden

The first thing is you have to do the work and learn at all the companies you're at. I would not be able to advise people on these sorts of things if I hadn't done the SDR role inbound and outbound and then done SMB, mid market and enterprise and seeing how it is zero to one landing your first 10 customers to one to five and five to 10 and 10 to 20. And there's a lot of different challenges that happen with that.

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Tyler Rachal

Yeah, it's basically being in the room is what you're saying. And really having had those experiences and then now with your business of fractional services as well as the coaching bit. I think a lot of people have those experiences, but you showed me your deck for Golden Ventures and I was really impressed with the way that you kind of packaged these experiences you've had into an actual sellable service. So I don't know if you have any tips on how did you land your first customer? Also one pain point that I know is prevalent with these types of businesses is sort of the act of setting of boundaries. You can, you can be a consultant/advisor for a business, but they'll treat you like a W2 employee in terms of their expectations of your time. I'm also curious, you know, how did you sort of package together as a business and how do you protect Frank Golden LLC from getting totally taken over by your clients?

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Frank Golden

Totally. So how I landed my first customers? Easy. Friends that wanted help and heard I was no longer at Airkit. So it was my previous employer, good friend, and amazing person, David Kelso, CTO and co-founder of Beyond. He said, Frank, I heard you're on the market. Do you want to help us out for a few hours? I said, sure. Income sounds nice, along with this little summer vacation. I didn't go into this really consciously. I took some time off, and then I had some inbounds from old friends that I worked with.

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That was my first client. That was the perfect first client because I knew who had built the sales team previously and knew the customers and knew the team. So it couldn't have been a better situation. And that went really well. We were together for eight months, hired new leadership, built up the team and they're doing fantastic. And then the next client was another former friend from Talkdesk. This guy, Daniel Latzman from Myndbend. And we worked together. And then shortly thereafter, I said, you know what, maybe there's something here. So I went to a few of my mentors and a few peers that have been doing this that I respect and asked them how they do it. I got a lot of different advice, hourly, retainer, number of clients, what to do, how to scope it. And then I just test and learn. So I've got, you know, got an agreement from a really nice guy, Travis Bryant, who I respect over in San Francisco, used to lead Optimizely sales. And he gave me a ton of help. And then I got a lot of referrals from my network and a friend, Ian Feeney, who runs a recruiting firm and fund.

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So with those channels, they just started having meetings offering to help founders with their earliest go-to-market challenges. And one conversation about like three hot button topics would turn into, ‘Hey, do you want to work together for a few months?’ And that's how it started.

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Mike Wu

I think there's a, there's a ton of wisdom in what you just shared and I kind of want to tease it out and make sure I'm, I'm, I'm catching the right things, Frank, but Tyler, you asked essentially like, how do you know what services to sell, especially as a consultant or a fractional CXO. And Frank, you essentially said like there was inbound. So you just listened to the market. People were coming to you and asking you, ‘Hey, how do you do this? How do you do this?’ And then that is what you crafted your services around. I think that's a really interesting point to call out. It's like there was already demand. People were coming to you meaning that's the expertise that you have, that they know you have, that they value. The market values that knowledge that you have, that experience you have. That's really good because I think sometimes having been a consultant before and knowing folks that have gone out to build businesses, sometimes you build something and, actually Tyler you and I have made this mistake before, you build something thinking that you can create some demand for it, whereas sometimes you just gotta listen to what the market wants and build something around that. And it sounds like that's kinda what you were doing, Frank.

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Frank Golden

Great point Mike. Kind of unconsciously but that's how it worked. It's like, here's your flow, where's the need, can I help them out? Okay great. Like could I have done some series B advising? Sure. Was I getting those opportunities and looks? No. Is it easier money? Maybe. But like for whatever reason this is the fit, listen to the market and it's been working.

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Tyler Rachal

Yeah, I want to expand on something you said. You mentioned that you're having these conversations with mostly founders and they're talking about their early go-to-market challenges. What are the top three to five challenges? And a follow-up is do they ever give you their challenges and you're like, that's not actually the problem. The problem is something else?

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Frank Golden

Yeah, sometimes. What I pride myself on is like everything comes from a good place, but I will be very direct and I will be honest, even if you don't like what you hear. The common challenges I hear from people Landing your first 10 customers and finding product-market fit. And I've worked with some clients where we do a three month engagement, have a ton of conversations and they say, you know what? I don't have product market fit. This is super helpful. I need to go back into build mode and pivot. So that’s the first one, finding product, market fit, landing your first 10 customers. 

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Second common one is most founders are technical, I'd say 80 % plus, and most haven't sold before. So if you're just able to be a true business partner to them and teach them how to sell, what best in class sales looks like, everything from from what's your ICP? How do you create a list of accounts and titles? How do you create messaging on which channels to engage those and have them take meetings? And then once you have a meeting, how do you run a meeting? Simple stuff that makes a big difference. Make these tweaks very quickly. So that's the second one is like how to run it. 

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And then the third one is how to hire the right founding salespeople. Sometimes founders don't know what to look for. There's a lot of conflicting advice out there and salespeople are generally good at selling themselves. And also this is a very hard role if you're going to to be the founding salesperson at any startup. So those are the three things I typically help founders with.

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Tyler Rachal

Yeah. And you've, you've been that before. What do you think it is about yourself that made you so effective in those situations being the first sales hire?

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Frank Golden

I mean, I still have this problem where I want to be more than just sales. And I feel like the earlier you go, the more that's true. So that's one of them. I like to be involved in the strategy, work with marketing, product engineering. I love having relationships with all those groups. And as you get larger, it's just not feasible always.

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Tyler Rachal

That's something that I've seen in very effective salespeople at early stage organizations. They're wonderful at relationship building across the entire company. And, and so, you know, when you go in and you pitch Morgan Stanley and you don't have this track record of 10 to 15 years in business, everybody has to play a role in winning that deal. You do not win that deal based on a deck. You win that, that deal based on meeting after meeting. And most of the time you're mostly impressing them with your people versus your product. Because the product is never fully there and I'd say that's something that comes across with you. You're just very genuine and that's something that I've definitely seen with successful salespeople at that stage. 

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Frank Golden

Yep. Thank you.

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Mike Wu

I want to ask you about the first thing you mentioned, the first 10 customers. Could you share with us more about the significance of that milestone for a company? Getting to 10 customers probably takes a lot of work, but what does that actually say about a company? Or what are you learning during that process of getting your first 10 logos?

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Frank Golden

You're learning so much and maybe nothing at all at the same time, but 10 customers to me means like early signal of product market fit, depending on how big the deals are, enough to raise an A and enough signal, hopefully from your champions and your buyers to identify where you should place your bets to go get the next 40 customers. And like, that's the biggest thing is like when you have three customers, you can do a mini ICP exercise and be like, who's buying our software? What are they buying? How much are they spending? Do you want more like/less like? If it's only three customers, when you have 10, it's like something and then you're like, okay, cool, Let's go run some tests and see what they come back with. So those are the two big milestones I think of informing your next 40 and then raising the next round. Oh, the last one is hiring your first rep. Like if you can take 10 as a founder, start considering what the first business hire / salesperson looks like.

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Tyler Rachal

Yeah. And when you, when you do look to make that first hire and I imagine this comes up with a lot of your current clients, what do you advise them on? It's kind of two parts, what do you look for in a first rep? And also how it's hard. That's a sale too, right? Selling that first rep. How do you convince someone to join a ship when the cupboards are all barren? There's nothing there.

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Frank Golden

So much goes into this. How do you convince someone to join a ship? First, like you have to be really open with what the role is, the ambiguity to it, how hard it's going to be. And you have to have those conversations with the candidate during the cycle. I listened to a Lemkin podcast, which was good about hiring your first few reps. And I agree with some of the stuff he said for me, I always look to hire the first rep as someone I know.

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Why? It's a known quantity, I've worked with this person, that ramp is faster. And the best VPs will have a bench of people that they'll bring with them. Great to lay the foundation, not great to scale because you want diversity of thought and everything else. So like, cool. Get your first two reps that you know, or your first rep that's a reference. Like at Airkit, we hired Connor Candito. Guy's a force to be reckoned with, doesn't take no for an answer, has seen multiple startups, tremendous business acumen, great relationship builder, both externally and internally, understands technology. Connor was able to prove that Airkit could be sold, you could sell a lot of Airkit in a year to a lot of big companies.

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So you need that person to build the foundation, because if you hire your first rep, and I tell people this all the time, and they don't overachieve their number, it's a really tough thing to build a culture on. Versus if you have two reps that are over 120 to 150% make a bunch of money. You're like, hey everyone, we're hiring more people. Here's the success that we can point to and you have a skinny playbook that shows what great looks like and what works and then it's just about finding the right people and onboarding them and enabling them.

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Tyler Rachal

That's incredible. I want to pause there because I think that's really powerful. There's a piece here because if you're a rep or let's say you're making that hire, that's one thing, but you've been advising these companies and I'll say as a founder, I find forecasting very hard in our early stage business. And you know, when it comes to sales, that's so important in terms of determining what the comp should look like. What are the targets they should be able to hit? So you mentioned getting to the 120%, which is effectively right above quota. Is there any way to think about that? Besides, do you give them a softball? What do you think about in terms of getting the right number for the reps, those initial reps?

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Frank Golden

I'm so happy you asked this, because so many of you don't know this and we didn't talk about this. The number that every founder needs to think about is what are my close rates? And that's from a qualified opportunity to deal one. What's my win rate? Win rates range between 15 and let's say like 50%. Okay, and let's just say your win rate is 25 % as an example. That's your win rate. The next number you need to know is your pipeline coverage. The pipeline coverage is the inverse of your win rate. So it's 4X. So I know as a rep, if my goal every month is 100K and our win rates are historically 25%, if I don't have 400K of active pipeline in a given month, I cannot reliably and confidently hit my number. And then you can roll that up across the team.

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But that's a common thing that founders need to be tracking. And the last thing is if your win rate is under 15%, do not go build more pipeline. Go figure out how to increase your win rates. Because it's tough to build a business off of 15 % win rates, especially when the top of funnel is even worse than that.

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Tyler Rachal

Somewhere there's a salesperson that's yelling like preach to this part. Because I feel as a founder, and I don't know if this is the same thing with your clients, but you're in this constant battle when it comes to pipeline and trying to figure out what your sales metrics, your KPI should be. You're in this battle between what is realistic with sales and also where you just want to go aspirationally as a business. 

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Commonly when I talk to tech founders, I feel like they're like, we need to get to 5 million ARR. And you're like, why? Because someone at Benchmark told us that we have to get to 5 million ARR. And they're just like, that's the number, right? Versus it being based on any truth. How much kind of coaching do you do with your founder clients in terms of giving them reality? You mentioned, hey, if your win rate is 15%, you got to figure out how to increase that. Do they fight you on that feedback?

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Frank Golden

They don't fight me on that feedback because at the end of the day it's their company. Like, you know, I'm just here advising. When I think about that, like annual planning and yes, I had a conversation this morning about annual planning and when you want to have very many customers, it's hard to do annual planning. So you have to have just an open and honest, direct dialogue about what is our goal and why is our goal that. What's the why behind the why? Okay, our goal is 1 .5 million. Why is it there? because we want to raise an A off of it. And because we're doing 500K right now, so that'd be a 3X. Okay, you want a 3X, that makes sense. You want to raise the A, that makes sense. Let's look at what we have in our current pipeline and if that's even feasible, because we have, let's say, six to nine month deal cycles. 

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So you look at that and you say, okay, we're at 500K, the gap's a million. And we have, how many months do we have to close that gap? What are the deals we have in play? Do we think we can source more deals? And you have to make something, especially in the early stages, that's achievable. The last thing you wanna do is miss your first sales goal. For company morale, for rep morale, so the rep thing I said goes to the company as well.

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Tyler Rachal

Totally. That makes sense. One thing I was going to touch on, you and I talked about this, so I'm going to kind of bring something from our personal conversations into the pod. But you made this comment about the landscape kind of changing in terms of equity for  employees, let's say go-to-market professionals, getting equity at a company, how that part of comp has changed dramatically and it might not be the same compelling sort of offer that it was before. I'm just kind of curious if you could describe what are some of the factors that go into that? How do you think about that? And if I'm a founder trying to make that first sales rep hire, what do I need to be thinking about in terms of my offer to kind of overcome that?

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Frank Golden

So there is a lot there. The first thing around equity in terms of how I look at it is I think about macro. So SaaS multiples used to be much higher a couple of years ago. Let's say they were 20X as an example, 20X revenue. Now they're probably half that. So in my scenario personally, if I was to go join a Series A startup as the VP of sales and get 1%, that 1 % has the multiple downwards compression on it. So, let's say we're doing $10 million in revenue at a 1 % on a 20 X multiple. That's $2 million. That's the value of my equity. That was two years ago. In today's world, it's worth 1 million because it's worth 100 million. So that's what I think about in terms of like, you're signing up to basically give your life to the startup for a couple of years. I think the average tenure for a VP sales is 18 months. If it goes better, it could be four years. And then you got to make sure it makes sense for you. 

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And I don't, I'm not an expert on the markets, are the multiples gonna get back up to 20? I don't know. So that's kind of why I'm sitting on the sideline here because I'm trying to figure out what to do and my advice to founders and I haven't seen this successfully yet, is in these types of markets if you find the right VP considering offering more equity than you might have two years ago. I think the equity bands are like one to two percent but maybe it's like two to four percent but I've heard of some of these trying to get that unsuccessfully. So I'm not a founder, but that's how I think about it.

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Tyler Rachal

You said the VPs tried to get that unsuccessful, like they weren't given more equity basically, or you said it was unsuccessful. The founders offering it, but it doesn't actually doesn't mean it's compelling to the VP.

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Frank Golden

I've had VPs like peers of mine try to make that pitch. You know what? Yeah, I'll do it, but I want 5%. And they’re like, no, no, no, not approved by the founder, not approved by the board.

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Mike Wu

Interesting yeah, I was just gonna ask you that Frank like if you're seeing that it happened yet. But it sounds like I could see that being really tough for a board or for a founding team to start that trend. But it makes sense, right? All like conventional wisdom would tell you for the right person it's always worth it. But just the points people are probably not used to seeing three or four percent.

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Tyler Rachal

Right, yeah. And I think to give a counter, founders have never been more uncertain about their futures. And I think when you look at equity, you look at that 1%. I'm not the guy to really break this down, I know people have talked about different ways that you can structure equity or doing profit shares or whatever. I know there's a bunch of different ways to think about it, but people have been questioning the traditional equity thing because you nailed it, right? You're talking about the average tenure is 18 months. So they'll, they'll vest a little bit, but that person's out the door of your company within 18 months and they still are holding onto a chunk of the company. And that's a chunk that you can't claw that back. So that means for the next hire, you're now down a little bit. That makes sense. So I think the founders because they're so uncertain about what their path forward is, I could see them being reluctant to give up more equity, even though the pitch for the right person totally makes sense. 

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I'm going to pivot here a little bit. You mentioned trends, right? So this is one trend, the whole kind of like, SaaS multiples, definitely being a big trend that's being discussed, but there's a million new trends in tech, AI being one of the biggest ones. And I'm just curious as someone who has been a part of a lot of high growth companies and now you're advising them, how do you look at the various trends in the market if you're advising your friend who's saying, I'm gonna join as sales hire number one at this company and they tell you what the company does, what makes you say, dude or dudette, sign on the bottom line as fast as you can or what makes you say I would maybe be cautious on this because this could be a flash in the pan sort of a bubble company?

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Frank Golden 

So two things there, one is AI and my view on that and the other is like my criteria to evaluate companies. The trend I've seen even 12 months that I've been doing this advising is like my first batch of clients were like a mix of B2B SaaS, maybe one AI client and my second and third batches almost entirely AI.

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Tyler Rachal

Interesting.

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Frank Golden

The other thing I saw is AI companies, the ones I've worked with, they either have incredible traction or trouble finding product-market fit. One example is like this startup I was selling into banks and they're having all these mid-market banks buy 100k plus deals in three months. I was like, how are you guys doing this? And they're like, well, their boards are telling them they have to invest in AI. So they're coming to us and they're buying faster than they've ever bought before. Wow, great place to be.

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So that's what I think about with AI. But the other thing on AI is like the smartest people that I ask about AI, VCs and people that run AI at big companies like Salesforce and Zendesk explain it to me as like companies previously where applications were built on databases today, they're applications built on LLMs and they don't know how it's going to shake out. I've heard that from three of the smartest people I know in this regard, which makes me feel like, okay, if they don't know, I sure as heck don't know. So let me just keep advising and like learning from all these AI companies I'm speaking with. And if anything is AI actually, it's the LLMs themselves. So I've had a friend or two join OpenAI or Anthropic and, yeah, you can get a job there. Cool. It's the next Facebook or Google maybe. So that's interesting. 

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But other than that, I don't know what to exactly make of it. In terms of criteria of companies that I look for, like for me personally, Early 30s, having done this experience, zero to 10, zero to 10, zero to 10, zero to 20, I would look for founding team that has done it before and exited, need to have product, not a nice to have, 10 million revenue minimum, best sales team I can find, top 1 % sales leadership, very strong signal that they have product-market fit, and potential exit opportunity near term.

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Mike Wu

That's a really good list.

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Tyler Rachal

That's a great list. And I think you mentioned to me as well, top tier investors. Are there any investors where when you see that logo, you're like, you got their money? That's a potential home run.

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Frank Golden

The name brand ones, but yeah, that's de-risked. So if you come to me and you're a founder, that's like raised from Excel, Andreessen, Felicis, like all the name brands, the top top de-risked off the bat and they have the money and they have the network. So it's, those engagements are obviously really exciting. But the same thing goes for the full-time role. Hopefully you're joining a company that's backed by some of the best investors because they have the highest hit rate.

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Mike Wu

Frank, can I ask you a third question about trends? So, you know, I follow a lot of sales folks on LinkedIn. And I think over the past couple years, there's been a lot of talk about how much sales has changed, go-to-market has changed. We've seen some things like teams getting just totally cut, like sales teams, go to market teams. The big thing is outbound is so different. But I want to know from your perspective, is go-to-market or sales more similar than it is different than, let's say, five, 10 years ago? When you're working with your clients, are the basics, the foundational things still the same or has it really changed drastically and we're like in a new day here where sales is done differently?

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Frank Golden

I think they are probably more similar than different. If any two things have changed it's sales is a bit harder than it was in the heyday of people making huge checks when everyone's just buying software and people like coming back down to reality. and then, the outbound is dead thing,  there's definitely some truth to that. I think the future of outbound will look like you'll have a centralized marketing slash sales ops team that controls all the outbound messages that are being sent and they're personalized because you're able to do that with new tools like Clay and all these other things. And you'll have much, much, much smaller SDR teams, like maybe 20 % of the size of an SDR team to do that personalization or to make phone calls on people that engage or to nudge along, do the work, be more strategic.

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And I've seen that happen at a buddy's company in Q4. He did that move and cut SDR head count by 80 % and had better metrics. So that I think is going to happen. Because SDRs are hard to hire, they're hard to have a promotion path. And at the end of the day, the channels are just inundated and saturated. So I don't see any new channels coming out. So how do you punch through the noise? Be more strategic. Actually, if anything's worked in the last four years, it's like sniper shots on your prospects. 

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Mike Wu

What do you mean by that? What's a sniper shot?

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Frank Golden

Like pick a list of 50 accounts that an AE and SDR wants to go after, get to know them really well, and then find your best shot in every single time, whether it's an investor, founder intro, very relevant personalized value add, and things like that. And that works for us. That's how we closed all these big logos that Airkit without having anyone know us. Everything was outbound.

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Mike Wu

Yeah, that's cool. The non scalable stuff, right? There was like a time where we're all talking about how do we scale this? How do we automate this and do more? And now it's like we've kind of come back. It's like, how do you just snipe?

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Tyler Rachal

Yeah, totally. I feel like oftentimes I'll talk to, you know, earlier stage founders and when they're talking about building up their pipeline, they just want to talk about the nuts and bolts of building like a spamming machine. like, how do I send a hundred thousand emails a day? And, I always tell people that this is going to sound insane, but if you send five highly personalized emails per day, you're basically some version of like a sniper shot. I put that up against the spam, especially for early stage companies. Spamming works when you've been in business for a long enough time and you're sitting on all this marketing lead data where you've got people that have attended things, downloaded white papers, blah, blah. But when you're just getting started, you have to really put your heart and soul into it. That's what people respond to. And those are the deals that actually close versus the spam stuff. So I couldn't agree with that more, the sniper shot approach.

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Frank Golden 

100%.

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Tyler Rachal

Yeah, I am curious. Just briefly is in this kind of changing sales team landscape. The SDR job at a minimum, It's getting reduced, right? You mentioned 20 % basically that the teams are 20 % the size that they were. I wonder if you were to talk to a young Frank Golden, if you think about how you got your start in sort of sales and go-to-market, what would you advise if you had a little nephew who's like, Frank, I'm about to graduate college. I saw what you did with all this cool experience at tech companies. They probably wouldn't say I want to be a go-to-market professional. Probably say, I just want to be whatever I want to make a lot of money, Frank. And I'm thinking about selling. How would you advise them? What's an entry level role that you would suggest they go after? How can they break into Silicon Valley like you did?

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Frank Golden

It depends on the stage and the person's preference, but we'll just assume it's early stage. Two things, find the team that's done it before and worked together before to de-risk as much as possible in the early stages. Two, find the best sales team that you can find. I'm talking about leaders, like people that are known to be best in class that you can learn from.

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Ideally you find a manager that's going to invest in you and help bring you up. That's so important early. And the third thing is to be in person. During Airkit, we had COVID and obviously that took us apart. But when we did get people to try to get back into the office, we had people where that was their first job as an SDR as being like, no, I think I'm more productive at home. And I was like, wait, but you've never worked in an office before. 

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Tyler Rachal

That's crazy.

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Frank Golden

And I just think you can learn so much more, build better relationships, dramatically increase the velocity of your career if you're doing it in person in the early days.

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Tyler Rachal

Yeah, It's funny. I never thought I'd say this. I long for the days when every office, especially the sales floor, was all about that gong, right? You had like someone had a gong or a bell or like a big robot, you know, there was a time where that was kind of like a punchline of like that show Silicon Valley. But now I'm like, man, take me back to the gong days. Take me back to you close that deal on a Friday and people are like, beers at 4:30 or whatever it is. I'm going to sound really old here. I think the youth is definitely missing out here. I hope there's some type of cyclical nature. I hope we come back to that, but who knows? Because they have no interest.

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Frank Golden

Dude, I'll never forget like 2016 walking onto the Zenefits floor when Zenefits was like full bore in San Francisco. Walking down that floor with my buddy Spencer and there must have been 400 20 year olds on that floor. Every single person was sharing a desk. So two monitors and laptops to every desk. Wigs, dogs, footballs being thrown. I was like, what is this, Wolf of Wall Street? And then walking back I was like, this is insane. Yeah, that was like, that will always be imprinted in my mind of like, what the good days in SF looked like and you know, those times. Yeah. And now it's bringing people back into the office in SF, which is why a lot of people are coming to New York, which is interesting.

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Tyler Rachal

That is interesting. That's cool. Well, I have thoroughly just appreciated this. Appreciate your time, Frank. You've done so many incredible things and I want to land the plane here a bit with Golden Ventures. If there's anybody that ends up listening to one of these clips from what worked or listen to the full episode, you know, what types of companies are you looking to talk to? If somebody is going through X pain point, why should they reach out to you and all that jazz? And also, where can they find you? What's your preferred contact channel?

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Frank Golden 

Thank you. I really enjoyed this too. The short of it is if you're a founder, zero to one looking for quick coaching for yourself and then to hire your first rep could be a good fit. The second is if you're a founder in one to 10 million that needs fractional leadership for your AEs and SDRs could also be a good fit. I mentioned I work across SMB to enterprise and different verticals and things like that.

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How to get in touch. I work with five startups at a time to keep quality high. I'm typically at capacity and have an opening every month or two. So frank at golden.vc, my website's golden.vc, my LinkedIn's there, just get in touch and we'll have a conversation. If I can help you, I'll tell you. And if I can't, I'll tell you. But yeah, thank you guys.

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Tyler Rachal

Frank is, of course, as advertised. And also for anybody who's watching this video, you can see he's got a big old surfboard behind him. If you're also a founder, the likes of good hang. That's my version, people say great person to have a beer with, Frank, you're a great person that I would enjoy one to two feet, gravelly garbage day. And I would also enjoy three to five peeling, beautiful set waves coming through. You're just a good hang. So message Frank to talk about all things go-to-market, all things startups. This has been another great episode of What Worked, and we'll see you guys on the next one. Thank you, Frank.

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Mike Wu

Thanks Frank.

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Frank Golden

Thank you, Mike. See you guys.

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