Supercharging Enterprise Sales in a Downturn PT 1 | Andrew Phillips

Andrew Phillips


“When I first started at AWS in 2012, I calculated I needed to make 93 outbound attempts every day, based on estimated conversion rates, in order to get to my revenue goals.”

With a career spanning multiple technologies as they rose from obscurity to ubiquity, Andrew’s passion comes from developing and inspiring exceptional sales and go-to-market teams that work in the growth stages of complex and rapidly developing technology, often in highly regulated sectors or organisations. 

Andrew has been in technology for almost 25 years, starting out at Dell in 1999, VMware from 2008-12, then joining Amazon Web Services (AWS) in 2012 as the Public Sector Leader - ANZ and later as Public Sector Country Manager - ANZ, where he grew the team from just one (himself), to a team of over 110 people over 6 years. 

During Andrew’s time at AWS, he overachieved revenue targets in all 6 years – a run unmatched by any other country across AWS over that period. He also assisted to grow the business from A$137,000 in the first year to over A$210 million in the last year. 

Most recently, Andrew was Managing Director and Vice President of UiPath for ANZ, where his responsibility was to establish and grow both UiPath and the overall Robotic Process Automation (RPA) ecosystem in Australia and New Zealand. In his 3.5 years there he grew the business from ~$3m of ARR to $35m+ (13x), and the team to 140 people.

We sat down with Andrew to pick his brain and 20+ years of experience in enterprise sales, including how to hit revenue targets in a downturn, and what it takes to sell in complex and regulated industries as the little guy. There was so much gold, that we have broken it up into two articles. 

Andrew, let’s get started! In your opinion, what is the single most important part of enterprise sales?

“Good salespeople sell lots of product, but great salespeople make lots of customers successful.”  

Understanding how a technology works is just one step. Envisioning how that technology will solve a company’s unique problems, or allow them to pursue their business opportunities, requires a skillset that the product itself can not inherently do.

It is easy to forget that it is a person buying a technology, not an organisation. Taking the time to think deeply about how a new technology will impact that one individual's life is a crucial part of selling. At our human core, we are motivated to do things either out of fear (will this keep me safe…) or out of desire (will this improve my life and/or my company etc). 

While you have worked for large global companies, you have consistently joined at a time when they are ‘unknown’ either globally or in the Asia-Pacific region. How do you penetrate competing customer priorities with an unknown product?

It is a great question, there are two key things I typically advise early-stage companies I consult to:

  1. Don’t just go to the top, go wide “80% of selling happens once you have left the room”
  2. Enable your buyer to be the educator of your solution within their organisation

1. Don’t just go to the top, go wide “80% of selling happens once you have left the room”

Don’t just go to the top - 

A CIO at a large household name organisation once told me that he gets approached more than 12 times per day from Sales Reps who have solutions that could genuinely help his business, he just doesn’t have the time to entertain them all.

  • Aim for the people in the organisation that are ultimately going to benefit from the use of your solution and start there. They are usually not getting 12 approaches per day and are more likely to accept your contact. Map out the path to the ultimate decision maker/budget holder and start anywhere in the organisation that will eventually get you there. They often have the ear, and the trust, of the person you eventually want to meet with. There are no wasted calls in this approach. At worst you don’t get a call back but at best you get the attention of someone who has the attention of the person you ultimately want to get to.

Go wide – “How do I get as many people talking about the solution as possible?”.

  • In a typical firm with 100-500 employees, an average of 7 people are involved in most buying decisions (cited by Gartner Group). 5+ people typically sign off on each purchase (HBR
  • In an organisation you need to have several people understanding and explaining your solution, so go wide – to more than one person in the organisation. There may only be one ultimate decision maker, but they have multiple influencers within their organisation whose opinion they are much more likely to listen to than yours. Remember Sonny Vaccaro went to the agent, mother and ultimately Michael Jordan to win the contract for Nike Air. 


2. Enable your buyer to be the educator of your solution to finance, procurement, or their children

“If the person you are selling to can’t go and sell the solution to their grandparent, or the financial controller, you haven’t succeeded… despite the quality of your own pitch”.

Today’s successful Sales Reps are business translators. Their role is to explain the business benefits of a given technology to senior executives at organisations, especially when selling a product that is not well known or understood. Often, I see sales reps give an unbelievably detailed pitch, but if the person on the other side of the table then has to go and give a similar pitch to their stakeholders who may not be as deep in the tech stack, they often find it difficult to sell internally. Make it as easy as possible for them to be your internal salesperson within their company.

Think through what other material you can give to equip others to translate and educate their colleagues - 

  1. Send across shortened or simplified sales decks or send your original deck but with speaking notes as their guide– the speaking notes are not for you, speaking notes are for your advocate to explain the use case and solution within the organisation. The notes can jog their memory of the words and analogies you presented to them.
  2. Send across a deck that can be sent on internally and understood without it having to be presented – make it short, less than 5 slides. You can always include more detail in the back end of the presentation, but don’t rely on others reading it the whole way through.
  3. Provide a short explanation of the solution and impact – don’t rely on everyone reading or opening the deck. Lay out your unique value proposition in one or two sentences as that may be all that a busy executive reads.

What are the three things that you wished you knew at the start of your enterprise sales career?

  1. Never go a day without prospecting.
  2. You don’t sell to your customer; they buy from you.
  3. Long hours don’t lead to success, good hours do.

1. Never go a day without prospecting. 

~40% of Zoom’s revenue today goes into Sales and Marketing – no one is immune to sales.

I have always considered inbound leads generated from anything other than personal outbound prospecting by Sales Reps to be the cream on top. The Sales Rep still needs to bake the cake. Product Lead Growth (PLG) is a cost-effective model for early growth when the technology is strong and the business barriers to adoption are low but PLG-only growth into enterprise organisations is exceedingly rare. 

When I first started at AWS, it was only me selling to the Public Sector. I calculated the revenue I needed to generate to hit 150% of my quota and then worked back from there considering the conversion rate of meetings I could secure (which was very low at the time, maybe less than 10% and that was after I had secured the initial meeting). After some initial prospecting I calculated my conversion rate of outbound cold calls/emails/LinkedIn approaches to securing the initial meeting and from there calculated I needed to make 93 attempts every day to get to my revenue goal. In time, as the market matured and I honed my approach to selling cloud to the Public Sector, my conversion rate increased but this just meant I was able to generate more revenue, not that I needed to prospect less.

Even failed days bring you closer to successful ones. Even though prospecting is mostly dealing with rejection, all those rejections are steps towards an acceptance. Frame rejections as steps towards success and you’ll be excited about the No’s, not dejected.

2. You don’t sell to your customer; they buy from you.

It’s relatively easy to put yourself in another’s shoes but mostly we think of this as “How do I get them to XYZ?” If you think “What do I sound like to my customer? Would I take action from what this person just said?” you can start to approach things from their perspective and tailor your message to their individual needs and motivations.

3. Long hours don’t lead to success, good hours do.

I like to work in bursts that I have prepared for quickly and efficiently and then work without distraction on outbound activity. In sales, a minute of good execution is more valuable than an hour of good preparation.


Finally, what are the biggest mistakes in enterprise sales you see companies make?

There are three common mistakes we tend to witness when building out a sales function - 

Compromising on culture

The culture and the impression of your company is going to be set by the first few hires. Hiring a new seller is an opportunity to hire someone that will be a magnifier and multiplier of your company culture.

It is important to note the risk that comes with hiring your first salespeople. These people are inherently good at getting their point across, they’re selling themselves in the interview process. One of the easiest things that founders can ask their early Sales Rep to do, is - 

Ask them to - “pitch their current product to you.”

That is, instead of having them try and learn your company’s solution, one that they are not familiar with yet beyond publicly available research they have sourced, have them pitch to you the current solution they are selling. You will be better able to identify their ability to explain a product that is most likely foreign to you. This is a surer indicator of how well they may do with your prospective customers who are most likely not familiar with your technology. 

Hiring salespeople too early

Before building out your sales team, you should be developing your own skillset first. Salespeople are expensive if they succeed and expensive if they fail. Only once you have exhausted your own capabilities, should you move onto building out your sales function.

Not being transparent around the reasoning behind sales team compensation plan

Your sales compensation plan is one of the strongest levers you have as a leader to incentivise behaviour. It is important to explain to the sales team how the compensation plan aligns to the company’s financials and current point in the company’s lifecycle. Be extremely transparent on cash burn and the impact it will have on the company future. At early-stage start-ups especially, all employees should be motivated to increase the value of the company and that extends past an individual’s monthly compensation. Create a sense of trust and shared responsibility with your sales team by explaining how the sales compensation plan ties their success to the success of the company. 

Read more in the second part of this article - coming soon

Join the masterclass we are hosting with Andrew to give yourself an #unfairadvantage – register HERE