The average turnover rate for salespeople in high growth startups is now 34%. You hire reps, ramp them, and a third of them make quota. A tale as old as time.
What gives? Startup revenue leaders think they need to tweak the go-to-market process or implement shiny new tech, but there is often a much deeper, foundational issue. Too many revenue teams lack culture, mission, and values. The result is quota-grappling-chaos and missed opportunities. To succeed, salespeople must go beyond sales process compliance, beyond a sales playbook. In this talk, Sara will illustrate how defining the ‘how’ and ‘why’ of your early sales culture helps make the right thing easy to do.
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Alright. Great. Well, thank you for having me. It's lovely to see some smiling eyes and faces. I'm really pleased to be here in Edinburgh and speak at Turing Fast, which is one of my all time favorite conferences. By virtue of the content, excluding maybe this, we'll see, I'm acutely aware of the fact that I am the last thing between you and happy hour, but I aim to keep this interesting as it's a personal experience about the stress of leading sales and marketing teams and growing startups.
So throughout this presentation, you'll see a whole cast of characters. These are my lovely colleagues at Chartmogul, Marvin and Anthony here, but I've included some friendly faces that aren't here with me in person but are joined virtually. First, an obligatory about me slide, I am the head of sales at ChartMogul.
We help businesses grow faster using their recurring revenue, which means I can talk your ear off about any sort of North Star metric, annual run rate, lifetime value, churn, you name it. But today, we're gonna be talking about culture and talent. I am crazy about SaaS, love software, and I have been building a life in Germany for the last five years.
The last eight years though, I've been building commercial teams throughout Europe and the US. This is my dog, Morgan, and we're on a boat in the Chesapeake Bay. You'll see a few boats throughout this presentation. In my experience, I've collected a whole slew of experiences, some positive, some negative.
One such starts with a text from my VP of sales. I'm walking the New York high line a few sips into a cup of coffee and read this. Hey. Good morning, Sarah. Have the new sales rep send two hundred plus cold emails? This is a relatively new job and I get a bit of a sinking feeling in my gut, but I'm charged with some aggressive goals and I've just hired four new salespeople for a brand new office in New York.
So I respond with a, oy, okay. We don't have great contact information, but we'll do our best. His response, you'll figure it out. Stay late, buy them lunch, make it happen, to which I meet that with like a sassy thumbs up. I'm starting to feel a little frustrated, need a bit of coffee here, but I couple it with a we're on it because I really need this job and I've just hired a new team of people that are counting on me.
So this whole interaction leaves me feeling a bit sideways and I'm trying to figure out what to do next because I know that I am shortly headed to the office to ask a group of new hires to do something that a, we're not well resourced for, b, I don't have any evidence is going to yield the results that we need, and c, it's just not a good feeling because I know these customers, these folks that we might be reaching out to are part of our addressable market,
and I don't wanna burn these leads. We might need these customers to grow the business successfully in the long term, and is this really the right way to go about acquiring them? So all of this leaves me reflecting on something my very first sales trainer said, which is growth requires independent action under consistent pressure.
Now, giving you this presentation today from the perspective of a VP of sales, but admittedly, this is true for anyone that's responsible for helping a team or business grow month over month or quarter over quarter. You might be responsible for driving web traffic, marketing qualified leads, product adoption, or revenue, but at the end of the day, that pressure persists.
And that can be really tough, especially when faced with a pandemic where maybe your variable compensation or the money you take home is forty percent, fifty percent, a hundred percent up in the air, which is true for very many sales people. So I reflected on this a bit and realized that as it compounds and when it's sometimes coupled with a poor management or a poor product decision, it can result in something super intense like this.
These are glass door reviews that I've chosen just to stress the extremity of the situation, and they are totally the stuff of nightmares, much worse than the text I received from my head of sales. The reason that these particular glass door reviews are so stressful to me is because they attack the moral character of the business and the people leading those businesses.
Of course, you can see here actual company, not what they think, bad management, low moral fiber, built on a foundation of fear. I don't wanna work in any of these businesses. I'm sure you don't either. So what can we do about it? Well, over the course of the next twenty or so minutes, I'm going to suggest what kinds of strategies you might use to identify culture problems early on and to address them with a a few takeaways.
Shall we? Great. This is then the agenda, recognizing red flags, unhealthy behaviors in early stage startups. I'm a salesperson, so I'm going to deliver you my solution. And should you choose to implement it, I'll suggest how it might impact your business. I will give you some examples that don't include dogs but do include boats.
And then I have a framework for implementation. It's kind of my giveaway to you to sort of spur conversation within your own business. So I hope you've seen maybe some of these red flag tweets that are flying around the Internet. I chose a favorite of mine from Dolly Parton.
I thought, this sort of indicated her looking out for something, she says. When she sees someone whose beauty is beyond compare and auburn locks of hair, this sets off those red flags for her. And so I ask you what kinds of red flags should you be looking for in your business.
I'm just going to highlight five. Some are obvious, some are a bit more subtle, but my favorite is referenced by this road sign, which I saw a few years on a trip, change priorities ahead as an American, it really caught my eye. And so I was listening earlier to a talk that referenced OKRs and the speaker was saying, your OKRs are set on a quarterly or maybe biannually or yearly basis.
You're looking at them at intervals of periods that aren't too quick. Because if you're changing priorities quickly, folks are not gonna be able to keep up. Your mission needs to be relatively consistent. Your product vision and strategy needs to be relatively consistent. And should you continue to chase shiny objects, folks are gonna have a hard time understanding why they're doing what they're doing and being a part of that mission.
Let's look at the next red flag. This is an obvious one that's top of mind for a lot of folks. We're gonna talk a little bit about turnover later in this presentation. But if you're experiencing significant turnover, you're seeing that folks are staying for eight months, nine months, twelve months, it's really tough to move the needle in that period of time.
Also, a general lack of energy. This again, tough tough to diagnose in a remote environment where sometimes you can't see people and you can't understand what's going on with them. So keep an eye out for this. Constant gossiping or a lack of communication are also problematic.
This is particularly true for me. I lead a team a terminal with sixty folks, and we're all remote from Korea all the way to Vancouver. We've got folks in Greece and Croatia and everywhere. And so it's tough for me, I think, when things are quiet, does that mean the strategy is really clear and folks are executing?
Or does it mean that, you know, maybe they're slagging off of it and have Netflix on in the background? And so you have to check-in on these things as a regular basis to to sort of see where things are at. So next example here, red flag wise, is resisting experimentation.
Growth means taking risks, and if you find that folks are resistant to experimentation, it might mean a fear of reprisal, it might mean that they're not sure how to run experiments in a way that's going to be satisfying for the business and that they could use some help here.
Alternatively, over reliance on rules, hierarchies, and policies can also be problematic. This means that folks aren't empowered to do their work and they're looking to others to make decisions on a regular basis, which ultimately is probably slowing your growth down. And then to round out our examples here, everyone's favorite, which is culture defined by perks.
I like dogs and beer as much as the next person, but I don't work fifty hours a week for those things. I wanna be part of a company where I can make an impact and I can stay long term, know what I'm doing is making a difference for the team and for our customers.
So all of this thinking mostly throughout COVID had reflecting on, like, an early psychology lesson. I'm sure you're all familiar with some high school version of Maslow's hierarchy of needs, and arguably, Turing audience is so smart. There's probably someone here that knows more about that than me.
But this infographic on a Google search was super satisfying because it described really well what I was feeling as a leader. When folks don't have a sense of security, they're really hard to engage. It's tough to make those people feel comfortable and like they wanna work really hard to support those growth goals.
And so take the example of a salesperson. Maybe they're working from a shared flat and they have to make twenty, thirty phone calls to customers across Europe with international codes. If they don't have the equipment needed to do that, how can they feel like they're part of the organization and the goals have been set out for them?
So this is where my big first claim comes in, which is borrowed from the definition of ethics. Ethics essentially is systematizing, defending, and recommending concepts of right and wrong behavior. And so as leaders, it's really important that you figure out how to architect an environment where it's very clear what is right and wrong.
And this is why this interaction had me feeling so funky because I know I was headed to the office to ask people who were brand new to sales concepts of wrong behavior. And I was I was presenting these people with something that just wasn't good for the business, wasn't good for their careers, and needed to be resolved.
So maybe some of this seems obvious or at least non controversial, but what I'd like to argue here is that so very many businesses are focused on finding product market fit, finding go to market scalability that by the time these culture issues arise, it's really challenging to untangle them.
And when we look at the data around this, it's quite interesting because we see that the average startup is hiring that first HR hire around fifty employees. And so what that means is that early stage founders and executives really need to address these things early and people problems are tough.
And so while while this doesn't cost anything and and while it's going to spur some difficult conversations, it's something that I implore businesses to do to make to make the environment all that healthier. If not, what happens is accidental values. And so Harvard Business Review does this really nice description of accidental values.
They kind of crop up exactly that accidentally, spontaneously, and they are really just shared beliefs, values, experiences of the employees that work within the business. Now those accidental values can be great. Perhaps you've hired a group of people that values inclusivity and fosters an environment of competition or teamwork, but flip those same values on their head and they can turn very negative very quickly.
In fact, they might be exclusive or folks could be cutthroat and self serving or cutting corners in an effort to achieve your growth goals. Accidental values take hold and then they start to impact your business in the long run. It can result in employee turnover, lost revenue, and burned brand.
So you really need to address these things early because you don't wanna lose months or years just because you didn't wanna sit down and have conversations about what your business values. Let's look at another horrifying infographic. This is something that you might have seen, it's from an older Gong two thousand seventeen study and it's also the stuff of nightmares for people like me because the average tenure for a VP of sales is a mere nineteen months.
Turnover in sales generally is really high. Most high growth startups are losing thirty four percent of employees sales employees within the first year. And there's a lot of things that affect this infographic in particular, particular, but what I'd like to argue is that by implementing a system of right and wrong, implementing this strong foundation of values can really help you retain talent because nineteen months is hardly enough time to run a few sales cycles after getting up and running.
There's data that supports my hypothesis here from a founder circle two thousand nineteen report. When asked, folks say the main reason that they wanna join high growth startups is for the opportunity to make an impact. And I know that's true because I go to events like this and I talk to people here who want to have stories of firsts.
I implemented the first CRM. I signed the first annual customer. Additionally, folks wanna be part of a workplace culture that's supportive and that's no more true today than ever before as we reflect on what Brian said earlier in today's opening remarks. These are the same reasons we attract talent and the same reasons we retain talent.
We need to provide folks the chance to make an impact and a workplace culture that they want to be part of. So if I've lost you in the softer side of being an employer, let me remind you that turnover is very expensive. On average, losing an account executive is going to cost about a hundred thousand dollars and it doesn't take into account any of the time to recruit, time to ramp, and any of these lost conversations or deals when folks flip.
Not only are you losing out on revenue by losing great employees, but perhaps people are cutting corners. If you don't have a clear discounting strategy because it just didn't occur to you, you could have salespeople leaving as much as twenty or thirty percent every customer forever on the table.
And so if you leave people to their own devices, they're going to do whatever they think is needed to do the job, to get the goal, to hit the target, and it might not be in the best interest of your business long term.
On the flip side then, unnecessary approvals and oversight is going to mean that you might miss end of month or an end of quarter goal because I had asked my sales manager if fifteen percent for six months was an appropriate discount. What I'm trying to say here is that when it's not clear for individual operators to make an impact, you have lost deals, left revenue, and perhaps bad fit customers that are going to be bad for your business in the long run.
So my big second thesis then is defining the how and right of your start up culture makes it easy to do the right things. You want folks to be able to ostensibly look at any decision and say, based on how we operate, I feel confident that I'm making the best decision for the business.
Just because your team has created a culture, it doesn't mean it's the right one for your business to succeed. And so what that means is we need to impose a fundamental, strategically sound, and thoughtful, you know, set of beliefs on a broad group of people so that we can all get the job done.
Let's look at a few examples. This is again another boat. This is last time last time, rather, I was with my team in two thousand nineteen. We're in Majorca on an old Spanish Armada ship. I like boats. This is my hometown. It is in Annapolis, Maryland, and this creek is Spa Creek.
You can see a number of slips and mooring balls. It's actually the sailing capital of the world, and if you go there, I've got lots of great recommendations. But when I am in town, which I try to get there as much as I can, I volunteer with the harbor master's office?
The harbor master's office is a motley crew of fantastic folks. They're mostly hourly and seasonal employees, and they do this variety of weird things. They do fireworks for the fourth of July. They do environmental work. They do public safety work, and they're primarily high school, college age students that are working on an hourly basis.
And the reason I chose this example is because I wanted to take a little sidestep from tech, and I remember what it was like before the Harvard master's office put together some code of ethics. It was a lot of fun. Don't get me wrong.
It's great to wear shorts and get tips, you know, docking boats for for for big yachts in the Annapolis Harbor. But ultimately, the environment was not much beyond that. It was producing low revenue. There were corner cuttings in a way that I won't describe, and then there was also high turnover because folks were just there to to do the hours to get the tips, etcetera.
And so interestingly, this new leader came in and implemented a really strong sense of who this company was operated, and the results were pretty remarkable. We implemented then a safe environment. Boating can be very dangerous, especially when combined with hot summer days and alcohol and folks going in and out of the channel.
And so we reoriented the business around safety, around honesty and reliability, around helping customers at each interaction we had, and we became stewards of the city, stewards of the environment. And this this made for, you know, still the opportunity to have fun, but overall something holistically much better.
And so the result of this was that younger people, fourteen, fifteen, sixteen year olds, were able to make independent decisions based on what we had defined the business and how the business had been defined to operate. And so so many of them were were really thrilled by this.
They could take ownership of projects. One or two were actually featured in the local newspaper, and this allowed us to attract talent and to retain talent and build the brand. And then lastly, this cute little pig mentions that revenue is up a hundred and thirty percent is because we kind of got rid of a lot of the ******** and really started focusing on what made the business run.
And by stripping out a lot of the the nonsense and making it very clear what we were working on and why we were working on it, we were able to improve the revenue of the business overall. Okay. So back to the world of tech.
This is my team at Chartmogle. We have sort of our own version of this. We call it our sales compass, and ostensibly, it is like a litmus test. I implemented it when I first joined three years ago because I wanted the ability to hold up any sales interaction, examine it under the light, and say, did we behave the way that we want to?
And so there's just four tenets. I won't go over them in great detail, but my sales team is charged with making sure that they are aligned with the customer and the customer's business objectives. They are timely in their responses because it's our job to help the customer get to that business objective quickly.
We are credible about our product, about our industry, and about the offered integrations, and there's no excuse in sales to not be technically credible. That's something that I will go to the grave saying. And then we are valuable. We every time we interact with folks, we are creating value.
That's not bumping something up to the top of someone's inbox because it's convenient for you and you have an activity metric to help. It is really truly creating value at each of those customer touch points. Here's an example. Olivia is in the top right hand corner.
She's tough to see, but she was here with me in two thousand nineteen, and I just chose this screenshot because, a, I'm really proud to have worked with this fantastic salesperson for two and a half years, and I hope she stays for four or five years and helps our business grow.
And I'm really proud that she has a fearlessness about something that would scare the average salesperson, which is developer docs. Olivia is a salesperson by nature. She's not a trained computer scientist. She doesn't have a data science background, but she's absolutely willing to get into, in this case, the Ruby library and and the dev tutorial to show folks how to succeed with our product.
And so I think that's a testament to the sales compass that we've implemented, and it's really useful for us as we grow the business. This sales compass can be used in all areas of the business, not just like an individual customer interaction. Can be used in the way that we hire, in the way that we coach and do performance management, and even in the way we prospect and try to land new customers.
And so as I sort of wrap start to wrap here, I want to talk to you about how this might apply to your company or to your team. I'd ask you, is it easy for your team to do the right thing? I don't mean like, do they know what the North Star metric is?
I think you need these things in combination. You should have a North Star metric or some sort of revenue metric or customer value metric that you're driving for, but you also need some guidelines about how you get there. And so you can go through an exercise of doing this, and I would encourage you to do so by asking just five simple questions.
The first is, what does your team value? Sit down with a core group of stakeholders. They could be executive leadership. They could be top performers. And ask those folks, what do you value? What do you value about working here? What do you value about the product, etcetera?
Next question. What do your customers value? So go through that same conversation and then hold those two things up next to one another. How do they overlap? Are there things that your customers considering very important that your team totally overlooked? Do you need to address that somehow?
And when you go through this exercise of values, I'm not talking about a mission statement, I'm not talking about anything like that, I'm talking about really, like, how you operate. I want you to choose descriptive and unique descriptive values are easy to remember.
If I say, you're hardworking, I'd be like, blah, boring. Choose something else. I want you to choose descriptive values because you need to have a conversation about what they really mean. When we talk about the value hardworking, what my hardworking is is different than your hardworking.
And so we have to come to a consensus on how these values can act within our business because our own unique experiences inform the way we think about these abstract concepts. So the third question comes after this slide because I wanted to share with you an example of Amazon's leadership principles.
This is something that I just I go over every couple of months just because I find it quite interesting. There's too many. There's, like, fourteen. I can't remember them all, but I really like that they are actually in conflict. Some of them are in conflict to one another.
So just choose two, for example. Right? Bias for action and dive deep. Now when Amazon implemented these leadership principles, they started to do it in part to to inspire conversation. And so when someone makes a decision, you know, how do they how do they back that up?
How do they think about it? And how do they attack that kinds of problem solving that's required to grow the business? And so there's plenty you can read about this particular topic and would encourage you to do so. But here's question three. What are your metrics of success?
Now in my role at Chartmogul, I live and breathe metrics. I know a sad amount of acronyms, but metrics of success are different based on your business and your department. I've chosen three, like, very simple examples. One is time to value, the other is growth rate, and the other is NPS.
You should probably ask this question not just for your business, but for your customers as well. What do they value? Do that exact same thing that I just mentioned, which is compare what you value as measures of success and what your customers value as measures of success.
And then the fourth question then is what what are your standards of quality? So I had a boss. He he said something that kinda, like, rubbed me the, like, rubbed me the wrong way a little bit. He said, I'll know remarkable when I see it.
And I was like, that doesn't give me much to work with. Okay. I'll give it a go. And so I like this question because it lets you get prescriptive about what a good piece of work looks like. Mailchimp does a really nice job of this.
I've loved their example of this content style guide because it's decisive, it's opinionated, but it's clear. And and then you're not faced with that that funky interaction where it's like, okay. How about how about this? Do you like this? And your boss is like, nope. Not that. Try again.
So here are some examples of of what I mean. Perhaps you want to determine the success of something by its completeness or its accuracy. This might depend on the environment you're in. If you're in, like, a highly regulated environment or highly technical or specific environment, I I suspect that accuracy is really important.
If you're in an early stage growth growth company, maybe you want something that's fungible, something that's reusable and repurposable throughout the business. Brand is certainly something to consider. And the fifth example I have here is, have you considered risk and have you addressed it?
I really like when people come, have already thought about, okay. I have this really good idea. I'm thinking about doing this. Here's here's what could go wrong. Here's how I'm gonna overcome that. So so these are some considerations for you. And then finally, ask your team, how do you lead by example?
I suspect that there are some top performers or some folks that really just outshine the rest, and so you can take a look at who those folks are and what are they doing and how can you replicate it across the business. So these are the five questions that we just went through.
The first is, what does your team value? What does your customers value? How do those things compare and what do they mean for how you should operate? What are your metrics of success, your standards of quality? And then how do you lead by example?
So go through this exercise and have this conversation. Don't wait until you hire an HR person and pay them a lot of money to solve your people problems. Make it very clear for folks to make the right decisions based on having these conversations.
And then use them. Use them regularly. Use them throughout your business. Don't set it and forget it like anything. Use it in your hiring. Use it in your performance management. One book recommendation quickly before we part is traction on demand by Gino Wickman.
He offers this great series. Concept is called the entrepreneur's operating system. It's all about developing an operating system on which your business can run. So you can kinda, like, not set it and forget it, but you can reuse the same tools to to keep the business running without creating excruciating stress.
And this is a screenshot from a a from a a tool that they give you in this book. It's really fantastic. And they basically allow you to assess individuals or teams based on how they're living that standard of ethics that you've set forth, and they use this perhaps in performance management and things.
So finally, just to do our key takeaways then, and I will release you to to the coffee, to the tea, to the wine, what have you. Remember that growth requires independent action under consistent pressure, and don't let that pressure compound and get the best of you.
Growing a business is a hard thing. That's why we enjoy coming to conferences like this and enjoying each other's successes and each other's miseries. Address those things with conscientious leadership, and don't just do it about your product market fit and how you're gonna appease your investors and how you're gonna improve your valuation.
Do it about how you want the business to operate so that when you go home every day, you feel good about the customer and colleague interactions you've had. So define the how and why of your startup culture to make it easy to do the right thing.
And if you wanna talk to me about this or SaaS metrics, I'm here for the next two days. Thank you so much for your time.
