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THow to Get Started With Sales as a Startup Founder [Interview with Whitney Sales]

Forster Perelsztejn author on Overloop the sales engagement, cold email, and LinkedIn automation software blog
Forster Perelsztejn Feb 6, 201810 min read

Whitney Sales is a startup sales expert and coach based in San Francisco.

She took the time to talk about the do's and dont's of sales in a startup environment and recommends a few tools might need to kickstart your endeavours.

Check out her resources for startup founders!

Thanks for doing this. Could you start by introducing yourself ?

Thanks for having me! My name is Whitney Sales. I’m a general partner at Acceleprise, a 4-month long, B2B SaaS accelerator based in San Francisco with programs launching this year in New York City and Melbourne, Australia. We invest in and work with pre-seed to seed stage enterprise SaaS startups. I’m also the CEO of a company called The Sales Method where we offer a market framework that helps founders clearly and systematically map their go-to-market.

From your experience, what are the most common mistakes you catch startups doing when it comes to sales?

One of the biggest issues I see early on is the founder trying to hire a salesperson instead of doing the selling themselves. It's critical for a CEO to know how to sell. They're going to be selling their company when they're raising money. They're selling their ideas when they're pivoting to their board and their internal team. And they're selling the vision when they're hiring.

They're touching all aspects of sales, and if the CEO doesn't think they're selling, they're crazy. Learning how to sell your product early on is important because you need to serve as that bridge between your customer and your product and really understand what your go-to-market is going to look like, not just what product you need to be building. It's kind of a two-fold role as a CEO. Selling your product is not only knowing the direction of the product. It's also knowing how to actually take it to market, and it's a really critical role for a founder to take on.

The second one I see most frequently is hiring a salesperson rather than a sales development representative. Meaning someone who basically serves as a support person for the CEO while they're selling. It's usually a more junior person, so they're a bit more flexible than management They don't have a set way that they're used to being managed. It helps the CEO get their feet underneath them and takes some of the more administrative tasks off their plate.

An added bonus here is that when the CEO does end up making their first sales hire, they have someone to support them in training that sales person and supporting them as they ramp up.

It's also knowing how to set your sales person up for success. We’ll often see the CEO hires someone, put them up for a quota that they think they should hit, but the quota's designed in an arbitrary way. Founders and CEOs often need to take more time setting expectations and training their first hires to avoid losing them early on.

I imagine that selling a startup product is not the same as selling a big company product, especially as the owner. What are the differences between selling at a startup and at a big company?

There are a lot of differences. The biggest one depends on the stage of the startup. If you're one of the first sales representatives, you're really striking new ground. The CEO may be the only person selling the product when you join a company, but CEOs sell very differently from a sales person. You're really going to be establishing a lot of the processes for selling your product as an employee vs a CEO.

The second thing is in regards to your market. If it's an established market, as a startup, you're coming in as the incumbent, and you have to have a very strong reason for replacing the status quo. The value that you're establishing has to be much, much clearer, and much stronger because your customers are taking a risk by buying your product.

If you're a new market, aka there hasn’t been existing products solving the same problem in a similar way, you’re really breaking new ground. There won’t be established budgets or needs. You have to create them and help your customers sell your product internally. It ends up being a much more creative sell and usually takes a longer time.

At what point in product development should startups start selling?

You should start selling as soon as possible. Every conversation you have is a sales conversation. It just depends on what you're selling the customer on. The sooner you can start associating value with that deal, the sooner you actually understand the true value of your product, and you also start to understand your go-to-market strategy. The problem with waiting is you're really not going to understand who your target customers are.

There's a pretty clear process. What do your target customers look like, externally? Who are the internal buyers within those organizations? How do you talk about your product effectively, so they understand it? What are the value propositions for your product, so the benefits to those organizations? How do those companies buy new products, so how to they learn about them and then buy them, and then what are your potential channels, and what potential pricing model can you put into play?

You won't find any of those out unless you start talking to your customers, and associating value with those conversations is really when you start to understand whether or not you have good product/market fit. Customers may be using your product, but if they're not paying for it, you don't necessarily know if you've established a really clear product/market fit. It doesn't necessarily mean tying money to it. It just means tying value of some sort to it. Tying a brand's time, or money, or name to it, and associating some of those values with it, so that you have the ability to prove out your model and get to market is going to be really important.

Let's talk about sales management. When you bridge the gap as a VP of sales with companies, how do you define your mission towards the organization and towards the sales team you're working with?

When I start working with a sales team, early on, what I usually do is sit down and understanding what the strengths and weaknesses of the organization are. It's also about understanding its culture.

Then, it's looking at the individuals and the strengths and weaknesses of the team. Sometimes, sales teams are really great at KPIs, but they lose some of the soft skills that are really important, so they're driving the team on KPIs, but they're not enabling them for success or vice versa. So it's finding the proper balance between those two for a company.

We'll then start looking at the areas to innovate. One thing I do when I'm in a full-time role consulting, or at least two to three days a week, is we'll sit down and do a sales innovation round table. It's looking at what are the things we're doing multiple times a day are, and how can we use technology to cut down the time those take. We start looking at how we are doing these things, and how we could be doing them better.

Awesome! On your LinkedIn profile, it says you assess the teams in recruitment, so how do you attract talents to an organization?

It depends on the stage of an organization. Most of the time, the first sales hire will come through my network, or come through the CEOs network.

The second is through networking. It's easier because people will know you, so there's a lot less selling that needs to happen if somebody knows and vets you, and can introduce you directly, especially if it's not someone you know directly.

Your first couple of people should be vetted for a couple of different areas and one in particular being previous experience. Have they worked in early stage sales before and were they successful?

From there, once you have three to five reps under you, you probably have a leadership team in place. And at this point, those people should have a network they can bring in of established reps they've worked with before. And you should have enough traction that you did your second raise, so typically, you've reached Series A at this point.

A lot of it has to do with selling the vision of the company. The first couple of hires are usually the hardest, and it's easier if you can find those through your network and via referral.

There are more and more millennials entering the workforce, so do you see them as a better fit to work in tech startups, or do more mature and experienced profiles make more sense?

It depends on the role that you're hiring for. If you're an early stage tech company with young founders, you may want some more senior people on the team who have deeper domain expertise. You may have uncovered a gem in the market, but you also need to surround yourself with people who understand your market really well and balance that. If you're a more established, older leadership team, then yeah, you want some younger talent.

Younger people are great for selling new tech, like marketing tech, HR tech, sales tech, a lot of the AI tools that exist today, drones, because they grew up in a generation where those things are just kind of established.

Some of the older markets where the relationship is more valued, and the more old school way of doing things is the way they do them. You need people to adapt to that way of doing things as well. Find a balance around how your market buys and then find the people that fit the culture of that market.

Since you're an advocate of automation, what's your sales stack? What tools do you use and/or recommend?

Those vary across the board. It depends on the organization and what stage they're at. Duck Soup and ZenProspect are really good. There's a number of Chrome plugins. I use BuiltWith all the time. Datanyze is great for that as well. Boomerang's a great tool. Calendly is also great. I also have an account merge system that I use because I have five different calendars across everything that I do, so I’ve got a bunch of stuff I need merged together.

You need Linkedin Sales Navigator and SalesForce is the go to for sales CRMs. There's also a cool company called Affinity that's coming out.

You need to keep an eye on some new tools and you can't get too attached to anything because then you're not willing to innovate.

Alright, you've already given a ton of advice today! If you had just one piece of advice to give right now, what would it be?

The base thing that I’d tell anyone, and it's something that I had a hard time with early in my career, was just trying things. Just try it. You don't know if it's going to work unless you try it, and there's always lower space to try everything, so it's better to try something and see it not work, try it a couple of times, than it is to not try something and fail, or not do as well as you could do.

One of my biggest fears as a salesperson early on was messing up the opportunity. As a sales leader, just being transparent. It was really difficult. I was like oh, this is how I'm supposed to do it, versus just being myself and figuring out my way of doing things. But a lot of it had to do with just learning to try things. I had to realize I'm not always going to have the answer. I don't have to have the answer to utilize my team and just try things. The more minds, the better.