My Journey To HowNow’s Head Of Sales: Building And Growing A Sales Team

Gary Stringer
June 23, 2023
July 20, 2023
Team HowNow

🤔 What’s the career journey of a Head of Sales like?

🧑‍🤝‍🧑 How do you grow a sales team and build more structure when you join a startup?

🤝 What qualities make a great sales rep in a fast-changing world?

We put these questions and a few more to Chris Chesterman, Head of Sales at HowNow, and here’s his story…

Chris, tell us about your background and career. Where did it start and how did you end up in sales in the first place?

I actually originally did a degree in industrial design. And the whole premise was that someone gave you a challenge or a specification of something they needed, then you had to kind of interrogate them, understand what they wanted and then design a solution.

Usually, you design a couple of options and pitch it back to them. And that is effectively the kind of the tenuous link I made between my original degree and what I went on to do.

But what it did give me a real passion for was getting to know people and understanding why the heck they have a problem. What’s the real human context behind it, and then how do we try and find a solution to help them move forward?

That is a mantra I’ve tried to maintain throughout my career.

Once you got into that first sales role, what was that like, and how did it progress from there?

My first job in sales was at a company called Build Online down in Maidenhead, which was like a proper bootstrap startup trying to break into the construction world.

“I was there doing 80 to 100 cold calls a day, and it was a very rude awakening to the reality of what’s required to build up that maturity to handle lots and lots of difficult conversations, to manage your time, and motivate yourself over and over and over again.”

And beyond that, I progressed into a typical kind of AE role with a company called Opel Telecom. From there, I then actually got headhunted by Pearson, which is very interesting because Pearson is now one of the biggest investors in HowNow.

What’s the biggest lesson you’ve learned over the course of your career?

It probably took me a decade to realise it in truth. But when I first got into sales, I thought it was all the things you associate with sales naturally: you need to be disgracefully confident in everything you say, a little bit arrogant, and that it’s actually all about pitching and selling.

“Sales is actually about listening and storytelling. And I think that was the huge flip for me, was the realisation that storytelling is how you bring things to life and help people envisage the value of whatever it may be that you’re talking about.”

If they can picture themselves using it and the impact it will have on them, they’ll champion whatever it may be.

Why HowNow? What was it that interested you about this challenge, and why was it the right time to get on board?

Great question, and it’s very simple for me! It comes down to two things.

One, what I saw was a sense of purpose, belief and identity that felt like something that we could really magnify. And it felt super credible! It’s something we can tell a truly believable story about.

And that comes from Nelson and Kuvera having a very clear vision, working with Ashish to deliver fantastic technology and translate that into a meaningful narrative that really felt like we were empowering L&D to have an impact. And that was truly exciting.

I’m also a bit of a techie and a bit of a nerd. And I love the fact that I genuinely think it’s great tech. It looks great. It really works well. We have incredible brands evangelising for us.

“I find it very conflicting running any sales organisation to be able to encourage and motivate anyone to sell something if I personally don’t believe in its ability to have the impact that we practise and preach.”

And what I said to Nelson a couple of times recently in terms of differentiating good companies and bad companies is would I recommend HowNow to my best friend as a place that they could come and work and should work?

Yes, absolutely. But equally, would I also go and sell it to my best friend if they ran a company and I wanted them to buy it? Yes, absolutely.

Thinking back to when you joined, there wasn’t necessarily the defined sales structure and we were lacking a Head of Sales, where did you start?

First thing first is to try and strip back any frustrations, emotions, processes, and talk to people, and I don’t mean that in a kind of cheesy way.

I wanted to understand everyone in the sales team’s why. Why do they still work for HowNow today? What is it that motivates them to come to work? And what do they want to achieve from work?

Chris Speaking at LT 23
Chris at Learning Technologies London 2023

By understanding that, I could start to work out a plan for how I support these people and empower them to hopefully be more successful.

And in terms of the sales processes themselves, what’s the story there?

I think it’s really critical to understand what’s frustrating or limiting people’s potential. Salespeople have a number of touch points in their daily working lives that really need to work super efficiently.

  1. Are we feeding them enough? In terms of do they have enough opportunity to really go and embrace and feel that they have an opportunity to achieve their goals?
  2. Are the processes and the technologies making things really efficient for them?
  3. Are they empowered to do the best work we could do? Are we giving them the materials and enabling them to execute to the best of their abilities?

By identifying those three things, we can build a foundation for success.

Was there one big priority you spotted by going through that process?

The more and more I dug into all of the things I just mentioned, I only identified one critical problem, and that was quite simply, we were not talking to enough people. It’s as simple as that.

Because of the great brand and so on, we’re actually blessed with pretty healthy inbound lead flow, which was good, and that was keeping people ticking over, but you’re never gonna hit your targets and exceed them if you’re just ticking over.

We effectively had two SDRs who were handling all the inbound and outbound, and that created a challenging balance in terms of how to prioritise time and where to focus. Now, the reality is if we’re not having enough conversations, it means that we’re not creating enough noise, we’re not engaging enough people.

So, we then doubled down and started hiring very emphatically around the outbound SDR functions, as part of the process where we actually segmented inbound and outbound. We had real mastery of the way that we are qualifying and managing our inbound pipeline, but then we also make sure that we have mastery in terms of outbound, bringing in the right calibre of talent and people and tools and process to really accelerate the outbound piece.

We’re speaking at the eight-month mark since you joined HowNow, how has the sales team evolved and what’s the long-term vision?

The team that I inherited in December was effectively a group of people whose roles were all kind of intermingled and there was a lack of focus and a lack of strategy. And it’s evolved a lot since then!

I think the first big milestone was to actually create what I would call structured expertise, going from a group of individuals that were all doing the same thing (a bit of inbound, outbound, mid-market and enterprise) to really breaking it down so everyone had the opportunity to show mastery in what they did.

So in terms of the structure, that will largely remain as is. However, there are a number of roles I believe we will really need in the future that we don’t necessarily have today.

For example, bringing in a team lead to champion the SDR team because that team will need to continue to scale as we maintain a ratio of SDR to AE that is really healthy in terms of how we go to market.

I want people to be able to feel like, even if I join as an inbound SDR and as my first job out of university, I can see three or four roles ahead of me within the HowNow sales team.

Finally, if you were talking to someone who’d never met our sales team before and was considering applying, what is it that you love about our sales team and culture?

I think we have some of the most remarkably passionate and intelligent salespeople I’ve ever worked with. And I mean intelligence in terms of their ability to read and understand customers, market conditions and internal structures, and come with really considered perspectives.

Team sales following up on LT leads
Meet our wonderful sales team!

And the most incredible thing about this sales team is that the feedback loop is so healthy. It never comes through a critical lens, but in the sense that, if we get together, I’m going to voice these three ideas, and we can find a solution to that together.

I’m trying to avoid the words like self-starter, but there is a reality that we need people who can manage their time, are very driven, and able to go and execute on the plan they’ve drafted.

A good HowNow sales teammate has that growth mindset! The environment, economy and context is always changing, so you have to be open to feedback, mistakes, and learning every day.

You have to be an emphatic storyteller too! If you can take three of the amazing things we do and translate that into how they’ll apply to someone’s day-to-day and help learning soar, you can help build that really compelling narrative on why HowNow will have a huge impact on them and their company.

If you’re interested in joining our fantastic sales team, check out our current vacancies here.