Hiring Salespeople: How to hire for technology startups

August 19, 2020 / Comments (0)


One of the biggest challenges I faced over my thirty-five-year entrepreneurial career was hiring salespeople.

As I have a sales background myself, I thought this would be easy…and most of my sales experience was in staffing and recruiting, so I thought it would be double easy!

And “easy” turned into an absolute nightmare!

Over the years I came to understand that the sales industry is full of people who simply cannot sell and here I mean in the pure sense of taking a product and selling it from scratch, with no established territories or any customer base.

This is what I term “real selling” and the type of sales mentality you need when you are looking at getting your startup off the ground.

Sure, there are many people with the labeling of a “salesperson,” but I am going to classify most of them as representatives, rather than pure salespeople…at least in relation to my own definition of “real selling.”

There are so many articles out there that explain the hiring process you can follow when it comes to hiring salespeople and it is not my intention to cover this aspect specifically but to outline my philosophy concerning selling your products and services as a tech-startup, which will give you my perspective of selling in general and how to generate profitable sales and secure long-term and valuable customers.

Too many companies go on a hiring spree and without creating their own sales culture — this will only lead to problems down the road as I have found out many times in my career.

It’s far easier to hire salespeople when you know exactly what you are selling and to whom and I’m not just talking about the products and/or services here, but the specific outcome(s) of what your product and services achieve and how you can articulate those to CEOs and executive leaders.

I have practiced what I preach and have made a ton of mistakes and they have been my learning curve in developing my own sales methodologies from my first sales job, selling home improvements door-to-door, and working my way up, selling into the boardrooms of some of the worlds leading tech companies.

Plus I co-founded a tech-software and services company in the depths of the technology recession in the late 90s early 2000s.

At that time, I was already the CEO of my main and successful global technology staffing company, which I had built from my living room in my South London apartment and you can read the story here of how I did it.

But I failed to use the strategy of that success when it came to the tech-startup and that was because of two things:

  • Fear…I thought I was out of my depth in such a high-tech environment
  • Technology — the company was too tech-heavy, with too much focus on the technology we produced and not the commercial outcomes that it enabled. 

Both these factors made life difficult and it’s easy to look back and use the exact science of hindsight, but this is why I started my blog — to share my journey and experiences, the good, bad, and the ugly in the hope that it will help and inspire yours.

And save you a few mistakes along the way!

Sales in a startup




It doesn’t matter if you are privately funded, looking for seed funding or further funding rounds, it is imperative that founders truly understand how to build the right sales strategy…the right way.

Sales are the first indicator of cash flow and in line with credit management, they are the two most critical components of startup success, so make sure you have these two issues covered.

Many startups fail simply because they don’t generate enough sales, or their sales cycles are too long.

I have been involved in startups from a few angles — investing in them, helping and advising, and companies that I have started or been part of starting.

It is essential that all founders of tech-startups develop and maintain a strong connection with sales, no matter what their backgrounds are.

And when I say connected, I mean dynamically connected.

It is not enough to attend sales meetings, or simply read sales reports…you have to understand and play a major part in developing and refining your sales strategy and to then get under the skin of it.

This will help you in the hiring process of all salespeople and everyone else for that matter, plus it will give you a handle on where your company is, in relation to your and investor expectations, if you have investors and also to make much faster decisions and pivot the business if necessary.

Creating the right strategy




A sales strategy for a startup must be:

  • Easy to formulate
  • Simple to execute 
  • Easy to measure

Many business plans address the areas of sales and marketing in a manner that is too complex.

The purpose of the business plan is to set out the expectations for the company, track the performance…and it should get everyone onto the same page!

I have written and plowed through so many startup business plans in my career and most of them (including the ones I used to write) don’t achieve the objectives.

What I learned over the years was:

  • Most are not thoroughly researched
  • Most will fall apart quickly
  • Most have totally unrealistic sales expectations

Make sure you make your business and sales plans simple, jargon-free, and realistic.

Write them, pull them apart and re-write them until you get it right…and workable.

My formula for sales success is to work from the top down — I target CEOs and executive leadership teams as I know that the decision-making process rests ultimately at that level, especially in this economic climate.

But there is a caveat to this approach — it takes more time.

When you are engaging at this level, it is easy to generate a great deal of interest, if your value proposition is compelling enough…but CEOs and executive leaders will then need to conduct the necessary due diligence and that means involving other people and often at lower levels.

You may be thinking that if this is the case, then why not start and win over the lower levels and work your way up to the top.

The “bottom-up” sales approach rarely works as people become naturally protective of their positions in a company and feel the need to exercise more control, plus they are not privy to the conversations and strategy discussions that occur at the top and that change budgets, spending and overall policy in a heartbeat.

It is tempting to go after “low-hanging fruit” and engage at a level in your target company at the level that brings in quick cash, but in my experience, it is a false economy and especially in this climate.

The right sales strategy involves making sure you have conducted deep research into your industry as a whole, then each of your target customers, to make sure you understand:

  • Ther vision, goals and objectives
  • Their commercial commitments or deliverables to their customers and how they differentiate from their competitors
  • Their financial performance, including a risk analysis

You need to think like an investor who has chosen an industry sector to invest in and then to research the specific companies in order to produce a target list for investment.

Only you are working to produce a target list to sell to.

It is important that founders conduct this research and remember the part about remaining dynamically connected to the sales process!

Take a look at this article: “Sales Training: How to become a key influencer,” where I go much deeper into the subject

Make sure that your business plan and has enough runway for your sales strategy to work.

Marketing — creating the right message




First, you have to build a solid foundation and that is to ensure you have the right message to deliver to your potential customers.

I made some major mistakes in this area when I co-founded a tech software and services company.

I focused far too much on the technology and its complexity — showcasing this in our company messaging and believing our customers would be delighted to partner with a company that had such a high-capability and technical offering.

In reality, they were not interested in the slightest and these were large multinational technology corporations.

I had not focussed on the one thing that they were crying out for…and that was simplicity.

The definition of genius is taking the complex and making it simple.

Albert Einstein

I should have listened to dear old Albert, but we entrepreneurs want to do things our way and often miss the “bloody obvious” as we say here in the UK.

If only I could turn back time!

The technology is of course extremely important, but that will come later in the sales process and many salespeople aim for a technical, rather than a commercial sales approach, which can lengthen sales cycles considerably as eventually, you will have to have a commercial discussion.

I prefer to start with a commercial discussion and then work back to the technology.

Make sure you have a clear, concise commercial message.

So your message, which is also your compelling value proposition is the core of everything in the company — it drives the culture, unites the people and it is the driver for sales.

Take a look at the message below from the company, ManyChat:

ManyChat is the #1 platform of Chat Marketing in the world. Starting in 2016, ManyChat has been used by hundreds of thousands of businesses worldwide for automating their Facebook Messenger Experience for their FB pages. With the ability to send SMS and Email now directly through ManyChat, businesses can create full automation sequences and reach their customers across multiple platforms.

This is what Chat Marketing is and what ManyChat is.

I trawled through about ten other companies, reading their messages until I came across ManyChat and some were full of jargon, others were rambling and I will tell you what I liked about the message from this company:

If you look at the highlighted words, you can see they are powerful — the #1 platform of Chat Marketing is an absolute statement and grabbed my attention from the start.

Starting in 2016, told me they had some years under their belt and hundreds of thousands of businesses worldwide gave me confidence.

Automating their Facebook Messenger Experience is again an absolute statement.

SMS and Email, plus create full automation sequences now bring in two other technologies…and across multiple


I have isolated the last statement This is what Chat Marketing is and what ManyChat is because it is extremely powerful.

They could have opened with that statement and built a huge campaign around that one statement alone.

If I wanted to be ultra-critical, then I would say that there is only one thing missing — the future.

The best sales strategies are the ones that take a customer through a journey…to a point in the future that shows them what could happen and the best salespeople walk them through that journey.

The future re-enforces the “now.”

The best companies are future-ready…now.

This gives their customers a subtle and unconscious message — they are ahead of the game, which gives the reassurance that what they provide now, was also thought about before today.

Take a leaf out of the ManyChat book and make sure that you create a strong business message…notice that they have a commercial focus and as a CEO or executive leader of a potential customer, the message would both resonate and be understood.

If you are the VP of sales for the company, all you have to do is put some commercial and data-driven benefits around the core message and then customize it to the customer, if this is necessary and you have a compelling value proposition.

Spending time in this area will lead to excellent rewards later and if you have created your message, take another look at it to make sure it is the best it can be right now — you will probably change it as you develop and that’s a good thing, but get it right so that your salespeople have the best chance.

Hiring salespeople




The hiring of salespeople should be a continuous process and that is because the failure rates are high for people working in sales…so you need a constant stream of options.

I am a great proponent of hiring people with an aptitude for selling, rather than established salespeople and that is simply because as a salesperson and entrepreneur, I would rather train people from scratch…and train them myself.

Over the years, this strategy has worked out the best for me in terms of return on investment, revenue production, and consistency.

That way, I can also create a sales culture that I have built from the ground up.

I would always have a sales-training program running throughout the year — the cost of this was negligible in comparison to the results, because out of every five trainees, I would on average, produce two successful salespeople.

Once I had got over the hurdle of the first training program, it was easy to have trainees shadow experienced salespeople and remember…I had created my own sales culture, defined my corporate message, and defined the exact people I would want those salespeople to contact in the target companies.

If you have the means to do this, then I strongly recommend this approach.

I never really trained my salespeople on how to sell, it was more about how to research companies and make an approach to the right people and at the right level.

When it came to the actual selling, they would accompany me, or one of my own leadership team, to learn in real-time.

You don’t “sell” to CEOs and executive leaders — you present a compelling value proposition that motivates them to buy.

I believe the dynamics of selling have changed…because people have wised-up to the sleazy sales tactics that still sadly exist and have far more information at their disposal to make informed and data-driven decisions, which is why you need a very specific methodology to sell to the executive leadership teams.

Here are some of the qualities I look for when it comes down to possessing the raw skills to succeed:

  • Fearlessness
  • Persistence
  • Creativity
  • Some form of evidence of entrepreneurial thinking
  • A degree of commercial awareness

Hard-working and exceptional communication skills are “given” and the ability to operate in social selling environments is crucial.

These are the raw qualities that I see as a “spark” and it is up to me to turn that spark into a flame and then a raging inferno!

Here is another consideration that many companies overlook, or they address it too late — reward.

I was always prepared to pay huge bonuses to successful salespeople and in my staffing company, my salespeople were some of the highest-paid in the industry.

It is essential to incentivize and incentives need to be tangible.

Equity is often dangled as the “carrot” in many startups, but you have to be careful here when it comes down to taxation and setting the right point for vesting — get specialist advice and make sure that your equity offer is realistic, achievable, and has a tangible value.

If you are going to go down the route of hiring experienced salespeople, then you need to determine two key factors:

  • Their ability to sell and track record
  • Who they are

There is a saying in the recruiting world explaining that you hire people for what they know and fire them for who they are.

I had the greatest difficulty in both of these areas and that is because, in reality, it is extremely difficult to determine either, especially in these days of data protection and the unwillingness of some employers to even give references.

But in any event, the good salespeople will be proud to evidence their performance and they will also be comfortable in social environments and this is where you can get a much better handle as to the “who they are” aspect.

I have had some disastrous social meetings where I have been initially impressed with the person at the interview stages and then witnessed them not be able to handle a couple of drinks in a social gathering that I invited them to attend to meet some of the team after work.

Thankfully I found out sooner rather than later!

My advice to any startup is to make sure you have the right advisors in place to help you navigate through the process.

Here is an article from Hubspot that may help you.

If you do not have the experience to do it yourself, then I would suggest you get the help of an expert who can advise you, whether that is for the short, medium, or longer-term, the right advisors will save you far more money than they cost.

Finally, selling is not complicated — it’s the people involved that make it complicated and with the sales training industry worth over $4 billion, there are plenty of people and companies willing to put their own spin on things, which only serve to increase the complexity.

Remember…you as a founder or co-founder must research and stay connected to the process, work on nailing the corporate message, and then contact your customers at the highest level!

If you need any help in this area, or you have any questions, then please do not hesitate to get in touch with me:


Neil Franklin

Neil Franklin-Sales-Training-Entrepreneur

Last modified: September 8, 2020

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