This is the second part of our interview with Ben Wright, one of the early employees of Ariba, staying with them through their IPO. We ask further questions on the lessons learnt from his experience and how he now imparts this knowledge and expertise into current start-up and scale-up companies.

Do you feel there is a tendency for tech start-ups to overlook the importance of having an established and clear sales strategy?

​For early stage startups – and by that I mean pre-Series A – the biggest mistake I see being made in sales and marketing is not enough experimentation. I can’t tell you the number of companies I’ve seen pick one go-to-market strategy because it seems the best option at the time and they just keep ploughing down that road, spending more money on it even when it’s not delivering the results.

Early stage startups do a great job of iteratively building out their product, starting with early demos, getting feedback, iterating into an MVP, getting more feedback, changing, adapting, iterating, etc etc. ​What they often don’t do is to take this same iterative approach and bake it into the rest of the business, particularly the sales and marketing side. And it’s really important that they do that pre-Series A, because once you’ve raised a Series A you’re on the revenue treadmill and if you find your GTM strategy isn’t working then, things will get quite choppy.

As you head into Series A and beyond, it then becomes really important to have a clearly articulated sales process that everyone is following – and to continue with the iterative approach, making sure you’re constantly reviewing wins and losses (losses always tell you more than wins) to keep improving your sales process.

A lot of sales teams I’ve worked with, they have no Sales Playbook and their sales people are all off selling in different ways with different strategies. While I want innovation from my sales team to help improve whatever we know is the best practice of the time, it’s also really important they everyone is following the current best practice, qualifying deals the same way, asking the right questions in customer discovering, handling objections the best way, handling stakeholder engagement the best way we know, putting proposals together in the same way.

Otherwise it’d be like running a kitchen by hiring a bunch of chefs, giving them the menu and telling them to make 100 meals a night. No recipes, no ingredients, no process. It’d be chaos, you’d get all different sorts of meals at all different times with all different sorts of flavours and qualities. And yet that’s exactly how a lot of startup sales teams are run and it’s no surprise when they miss their numbers.

So you need to put a sales methodology in place, create a Playbook, create a coaching plan, and train your sales people in the best practice – that you know of at the time – at every single stage of the sales process. And do the same for onboarding new sales people. The ‘shadowing’ approach of getting new sales people to follow a couple of your existing sales people just doesn’t work. You need to train them in your sales methodology, giving them the right resources and ensuring they have at least a good competency at every single stage of the sales cycle. Run workshops, do role playing, listen in on calls, sit in on meetings – put a structured programme together to make this happen and give them a Playbook and associated resources, and follow this up with a structured coaching plan.

Having experienced working for a very fast growth company, what are the key factors in a company scaling rapidly and successfully?

Firstly, it’s all about the people. You’ve got to approach your hiring by constantly looking for people who are better than you. Smarter, faster, more energetic, more determined, more persistent, more drive, better domain or technical knowledge etc etc. And it’s really important to bake that philosophy into the management team and have them bake it into their teams as they start to have managers underneath them. As soon as you start seeing anyone getting afraid of hiring people better than themselves you’ve got to take them to one side and call them on it. Help them understand that the success of the business is everyone’s success. If they’re worried about protecting their position – well if they are, they’re probably not a fit for your business – make sure they understand there’ll be enough senior roles around for all the great people as you grow. If they persist, you will have to let them go. It’s that simple.

And make sure you create a large enough option pool so that everyone gets stock options. Even the most junior people – perhaps especially the most junior people, as these are often the people who work hardest and have the most day to day stress. Everyone will be working their arses off as you scale, you’ll go through periods when you’ll need people to work 50, 60, 70 hour weeks and they need to understand you appreciate it, not just with words – which you should also make sure you use – but with a stake in the future of the business. When we went public at Ariba we had around 300 employees and every single one of them had options. And even afterwards, we tried to make sure everyone got options for as long as we could.

My last note on people is to hire your own Head of Talent as soon as you can to organise recruitment properly. Once you start scaling you’ll get overwhelmed by the number of people you’ll need to see to find the number of high-quality people you need to hire. Find someone with a great recruitment background in the startup world and hand the job to them. This will significantly improve your quality of hire as you scale.

Secondly, you need to make sure you’ve got your processes in place. Once you get product market fit, it’s all about the Playbook. I’ve already spoken about this on the sales side, but it’s important that you make sure every part of the business has their own version of a Playbook. Make sure your department heads are leading the charge on ensuring their Playbook is in place and is both being followed – by new and existing team members – and constantly iterated on to improve the best practice. Talk about it in management meetings, have different managers take you through their Playbooks, their training plans and their coaching plans to make sure they’re all keeping on top of this. Make this a priority.

Thirdly, as you scale, build regular Lightning Strikes into your yearly schedule – ideally a minimum of twice a year – to re-enforce your position as Category leader. It’s not enough to just establish your Category, you have to keep conditioning the market as you grow to understand and accept your vision of the Category’s future. A Lightning Strike is one of these events that keep you top of mind as Category King. It could be an acquisition, a product announcement, significant partner announcement, the hijack of an event or other major social media or PR event.

One of your Lightning Strikes could – in my view should – be a Dreamforce-style event, which sets you up as the Category leader with all of your partners, customers, prospects, press, analysts, influencers organised around you. This needs to start early, possibly as a form of Customer Advisory Council meeting or industry event run in conjunction with partners, which you will ensure morphs into an industry defining event with your company at it’s heart.

If you don’t know what I mean about a Dreamforce-style event, take a look at some of the keynote speeches from Dreamforce 2016 online – it’s a massive event for Salesforce where 170,000 people descend every year to worship at the altar of Salesforce in general and Mark Benioff in particular. There are plenty of things to not like about Benioff, and you’ll want to create your own tone of event that’s unique to your business, but the one thing I like about what he does is that no one who has any awareness of Dreamforce can be left in any doubt of who is the King of their Category.

It’s that feeling you’ll want your partners, prospects, customers, competitors, press etc to have as they walk away from your event. It tells your partners who they need to sign their allegiance to if they want to be successful, it helps prospects understand they want to get on board with your great New Thing right now, it sets the press up to write article after article about what they saw and it encourages your next round of potential financiers to get back to their offices and start warming up their partners to open their bank accounts for you. And it puts the fear of God into your competitors and potential competitors who go back to their offices thinking, ‘Shit!’. That’s what I want the output of your Lightning Strike event to be.

And as you roll through these Lightning Strikes you need to be constantly looking for ways of expanding your Category into new areas to continually increase your TAM. Be paranoid about becoming complacent. It’s so easy when you feel you’ve started to crack becoming a Category King to stick with what you know and it’s critical that your don’t – you should be constantly looking for new ways to expand your Category. Otherwise you’ll get to the point where the company starts to feel stale and people within and outside the company start to be less excited about what you do. And then value of your business will start to plateau.

And one last thing, just to be consistent about breaking my rule of three.

As Peter Thiel told Brian Chesky when he invested $150m in AirBnB:

‘Don’t fuck up the culture.’

From your combined experience to date, what key advice would you give to an early stage tech company? 

This may sounds obvious, but it’s something I often see being short-cut or even missed entirely. You have to understand – and I mean really understand – the pain your solution is taking away from your customers. This pain is the foundation of any Category you want to create and will be – should be – at the heart of everything that you do.

Understand this pain in as much detail as you possibly can – what exactly is the pain, how much does the pain cost your customers, how many potential customers have this pain, how many actually understand or are even aware they have this pain, what is it worth to them in monetary terms if you take this pain away, who in the organisation knows about this pain, how much detail do they know about the pain, how far up the management chain does the awareness of this pain go, does the board know about the pain, who’s responsibility is it to fix the pain, what other stakeholders are affected by this pain, how is the pain different across different sectors, across different sizes or types of companies.

If you come up short in the answers to any of these questions, you must do more investigation with your existing and potential customers until you have a complete handle on the pain that you are designing your company around removing.

Your understanding of this pain will inform virtually every aspect of your sales and marketing plans as well as your overarching Category strategy. Make it your mission to understand this pain better than anyone else in the market, better even than your customers themselves. Become the world expert in articulating this pain.

Articulating this pain in a clear, consistent and comprehensive way will set you up perfectly to create your Category and become the undisputed King of your Category.