Selling is hard work – full stop. Startups and growing companies find they need to tackle sales in different ways throughout their life cycles and there is no one-size-fits all to solving that challenge but there are traps for young players so this blog is for you and provides 3 steps to get you started if you choose to go down this path, and a challenge for founders whether this is the right path for them.


Setting the Scene

The journey leading to employment of a sales person often goes something like this – I-LOVE-MY-COMPANY Inc LLC is started by enthusiastic founders. These founders are usually subject matter experts with a strong idea and bundles of passionate energy. Being new and exciting, followed by a honeymoon period often takes I-LOVE-MY-COMPANY towards their initial sales targets before they hit a figurative wall – struggling to juggle the building and doing, investors, staff and other stakeholders with the time and energy required to SELL.

These founders, now exhausted and running on adrenaline, realise either a) sales isn’t their forte or b) their time is better spent doing the building and doing. A eureka moment decision is made to employ a sales person! sometimes that decision goes one step further and offers this new seller equity in the business so they have some perceived skin-in-the-game.

If you haven’t been a sales manager or business owner before the question of what happens next is all new territory. How does a startup or small business choose the right sales person for them? how do they manage this new seller while juggling a million different balls? what do they really want from this seller?

People who can sell are awesome but not all sales people are created equally and their motivations differ as do their styles, skills and experiences. To be brutally honest – good sellers can sell themselves well too so you need to be very prepared before interviewing for a role or finding yourself “sold” on a person rather than their track record. To help clarify what I mean by this I have written up a few case studies of what can go wrong.

What can go wrong?

These are 3 very real examples (with names changed) – so if you are reading your own story here, thank you 🙂

  1. Employing your cousin’s husband – Fred was really successful selling mattresses in Australia so knows loads about selling right?  Wrong. Fred has never sold Tech/Software/Services/Insurance/Anything-but-matteresses. Selling mattresses happens in-person, doesn’t require a network or hustling to get to the ultimate buyer, Fred may have the “gift of the gab” but that probably won’t translate for your business easily so Fred would need to be fed a great script and require plenty of support. The unfortunately outcome is Fred may never quite understand exactly what your company does let alone how to position your goods or services without you babysitting him on every sales call.
  2. Employing that really successful seller from <Global Vendor A> – Amy was hugely successful selling CRM software for Millions of $$, she bought a Porche off one deal alone last year so she will be perfect for my startup right? Wrong again. Global vendors have massive teams, mature systems, daily cadence calls, aggressive targets driving hunger with salaries at risk if not met, lead generation teams, pre-existing relationships with CEO’s and Chairs of boards….. Just because Amy was successful in that environment does not automatically mean she will be with a small/growing business without those conditions, she will likely flail, spend lots of your hard earned money on booze and coffee with little or no conversion.
  3. Employing cheap grads with no sales experience as your sales force – Dave and Jane both graduated top of their year in Marketing so will be great sellers for your growing business right? Sorry wrong again. Dave and Jane have no experience at all, they might have theory in Marketing, they might have endless energy but they have no idea how to walk through a sales process, how to close, how to guide a customer, how to read body-language etc etc. Equally you have never mentored a salesforce before, you have no processes in place to train and develop those skills, are running out of money and become impatient at their lack of sales – massive catch 22 there.

Now think about these scenario’s again when you are physically not in the same geographical location as your salesforce – these stories have happened to founders both with local and/or domestic sales people and with sellers forging their product or service into a new Country or new market too.

It’s not ALL doom and gloom I promise. It is possible to engage and motivate an effective salesforce for your company (in some but not all instances) if you create the right conditions and put in the work to educate, incent, motivate and drive them to success.

3 steps to get you started with a sales team


1. Know what they are selling

What does your service catalogue look like? clearly define the product lines

  • Be really clear – Product / Service / Price
  • Understand your cost model to run (build, support, maintain, enhance) your Products / Services. You need to be able to pay your salesforce within your Price too and you need to think hard about discounts and deals within that Price context.

What does your sales Collateral look like?

  • To be successful sellers need information, answers to every question, tools in their sales toolkit
  • Customer Persona’s and Value proposition messaging, website and collateral to send to / leave with prospects supporting your product claims

2. Know how are you paying them

Package is everything! it needs to work for I-LOVE-MY-COMPANY Inc LLC as well as Fred, Amy, Dave and Jane

  • Don’t ever pay a sales person 100% salary! ever! but how much you put at risk will drive their desperation too, so getting the mix of %Base / %Commission is so very important
  • Let them over achieve and reward them for growing your business with additional Commission or a bonus
  • Understand what motivates your sales people as individuals – one size does not fit all in this case
  • Equity is yours, give it away as a reward not an incentive
    • You put your house on the line for this business so think very hard before offering equity to an unproven (unproven in your context) seller
    • Equity is forever, what if they don’t succeed do you want to be buying them out in 6 months? or have a dormant shareholder? think hard about this one.

3. Know how are you managing them

Congratulations you are a sales manager now! Stepping up to your new role is a key to success for both yourself and your new salesforce

  • What systems and processes do you need to have in place to support both you and your sales force?
  • Make a decision on targets, stick to it, and manage to them – the first decision is what are they there to achieve: is it noise and leads? or closing deals? or establishing distribution channels? – you can’t have all of these at once salespeople need clarity of focus and goals
  • Will you manage for Activity or Performance outcomes? again pick one and stick to it

Put in the work and everyone will be successful

There is a lot of work involved in designing the environment for a seller to be successful and you as Sales Manager need to commit to the work required on your part to lead that success. It’s not insurmountable you just need to sign up for it and stick to it. You will need to be in essence a Player Coach.

I’ve meet Founders who give their sales staff 3 months before they start micro-managing or firing them, barely time to hit their strides, equally many of those same I-LOVE-MY-PRODUCT companies haven’t written Customer Persona’s or Value Proposition messaging for these newly minted sales staff. Really tough position to be successful from.

If you put in the work, support your team, clarify roles and targets both you and your sales force can be successful beyond your wildest dreams!

The Real Food For Thought is for Startup Founders – aren’t you, the Founder, really the best person to be selling your Products / Services? you have the passion, know it inside out, have the autonomy to hustle to a deal and will be getting direct invaluable feedback from customers? perhaps in inside sales person generating leads and meetings is your first step? Think about that one for a minute. Good luck! Vic.

I love Dilbert for some reason, captures the essence of so many situations in my life. Enjoy these and go to for more – thanks.