10 Sales Strategies That Closed 100+ Australian Enterprise Customers & Generated Multi-Million Dollars In Revenue

As the Founder & CEO of my last tech venture, Contexti - a data analytics (big data/AI) company serving mid-market and large enterprise customers in Australia, I had to devise and execute a go-to-market strategy against a number of challenges.

Before starting this venture I had spent the previous 5 years living and working abroad in Silicon Valley, USA with another venture and I had started this business having no expertise in cloud, data analytics or data science.

So I was literally an outsider on all accounts, I was new (again) to the country and new to the industry.

To support our vision of being ‘AsiaPacific’s premier big data analytics company’ and our mission to ‘help customers create value from data’ , I had to figure out:

How do we get leads?

  • We did not have a large marketing budget
  • We did not want to cold-call prospects
  • We did not trust a ‘lead-generation’ service provider will do our brand and voice justice

How do we earn trust?

  • We were not known in the market as we were a new entrant
  • As the Founder & CEO I did not have any expertise in Data Science or Engineering
  • We would naturally be up against the safety of “No one got fired for buying IBM” mentality

What type of deals should we pitch?

  • Who do we sell to? (executive sponsor, economic buyer, business unit leader, practitioner, user, beneficiary)
  • What do we sell and in which order? (advice, consulting, training, product, managed service)
  • What risk, compliance, security, procurement and legal ‘trip-wires’ were we activating?

How do we close (complex) deals?

  • How do we navigate the politics between different internal stakeholders?
  • How do we position ourselves against (large, established) incumbents?
  • How do we create urgency?


From founding Contexti in 2012 to our exit in 2019 (acquired by Versent) we built our revenues from zero to multi-million dollars, securing and serving over 100 enterprise and mid-market businesses in Australia including Commonwealth Bank, Westpac, Suncorp, Woolworths, Seven West Media, Caltex, EFTPOS, Telstra, Optus, SAI Global, Quantium, Qudos Bank, Equifax, Sydney Water, Origin Energy, HealthDirect and Sportsbet.

Looking back there were a handful of strategies that enabled our success.

10 Sales Strategies

Here are 10 Strategies that I want to share with you that may inspire, support or challenge the go-to-market for your business:

1 - Tight Positioning

Narrow (tight) definition of what we do and who we do it for.

This also extended to articulating what and who we say “no” to.

In the early days we positioned ourselves for ‘big data analytics’ services and we took on work that had to do with Hadoop, Big Data, Fast Data and any initiative that supported Data Science and AI.

We’d say ‘no’ to any traditional financial analytics or traditional data warehouse work.

As we went on our journey, we tightened our positioning further to:

We serve:

  • Data Leaders
  • who are supporting a business transformation and
  • have identified data as an enabler of their future state
  • who have 5 or more data scientists and
  • who have self identified they need a cloud based data platform / data lake.

Tight positioning not only helps you to spot your ideal customer in a ‘sea of prospects’ but it also helps the market know clearly what you stand for.

2 - Own The Category

Brand association for anything related to ‘big data’ in the Australian market.

As audacious as it was, for a ‘startup’ who was also an ‘outsider’ to think they can ‘own the category’, it benefited us immensely to have this mindset and ‘act as if’ we were the category leaders.

This approach made its way into our sales and marketing strategies and communication, how we described ourselves internally to colleagues and future hires and how our partners were positioning us to their customers.

While there were many larger brands with much bigger presence, budgets and teams initially ‘flirting’ in our category (e.g Deloitte, Accenture, EY, PWC, KPMG, Capgemini, DXC) none of them had yet committed to the cloud, big data or AI categories in any serious way.

Some provided high level advice, but none at the time delivered any platform architecture design, implementation or support services - so we had a first mover / early mover opportunity and advantage.

Of course once the giants woke they played ‘catch up’ mostly via acquisitions but by that stage we had already benefited from the ‘let’s own the category’ mindset and ‘acting as if’ we were the category leaders.

 3 - Be Found

Let prospects find us by creating a pull strategy to bring people into the top of the sales funnel.

I dislike being cold-called. In fact if your number is not in my phone you will automatically (via a setting) get pushed to my voicemail.

Why would others be different ?

Additionally I did not have the time, budget or interest to educate or convince anyone that they needed our service.

I wanted qualified prospects to have self-identified they had a need and because we were the ‘category leaders’ they came to us for our help.

So one tactic that supported the ‘be found’ strategy was via premium content that created value for our industry and for our prospects.

For example:

  • We created the Big Data Maturity Model & Self Assessment - this not only became a lead magnet but helped establish credibility as being experts (category leaders) in the industry.

  • We launched the Big Data Centre of Excellence (sponsored by Cisco & Telstra), a physical space in Sydney CBD where we hosted free weekly morning business sessions (coffee & croissants) and evening technical meetups (beer & pizza) and invited outside speakers;

  • We launched the Show Innovation Podcast Series where we interviewed industry leaders including Kevin Bloch (CTO of Cisco), Catherine Stace (CEO of Cure Brain Cancer), Victor Dominello (Innovation Minister) and 30 others.

None of these initiatives ‘pitched’ anything, rather they were designed to be educational, inspirational and insightful and eventually drew qualified prospects to us.

 4 - Be The Customer Advocate

Be seen as a customer advocate, not a vendor.

There were a few tactics that helped us position as a customer advocate.

Firstly, once we got talking with prospects we did not try to ‘rush the sale’ or ‘close’. Our philosophy was they will buy when they are ready.

We were also vocal in communicating how this was deliberate and unlike the bigger incumbents, we did not have any ‘monthly or quarterly targets’ to report to an overseas head office. We gave our prospects the mental safety that we were there to work aligned to their priorities and timetable.

Secondly from our very first ‘sales meeting’ we ‘acted as if’ we were already their ‘paid trusted advisors’.

Most of our ‘sales meetings’ were like ‘workshops’ where we spent time on strategic whiteboarding, mapping their goals and exploring ways to help them overcome challenges.

We did not hold back on anything in those meetings in terms of sharing knowledge or insights.

Thirdly we did not have a single ‘product to sell’ we had multiple and sometimes competing products. While this quietly annoyed our technology partners this was seen by our prospects as being ‘product agnostic’.

5 - Reverse Engineer

Don’t sell, enable a purchase.

While we had our own firm (narrow) views on who we want to serve and how we want to serve them, when it came to selling (especially to larger enterprises) we became good at enabling them to purchase ‘what they wanted and how they wanted to buy it’.

This required intently listening to absorb :

  • How they describe their problem,
  • What they want from a solution,
  • What they think is the right approach,
  • Their intended timing and
  • The budgets they have allocated
  • What needs to happen to get sign off from legal, procurement and risk

Then ‘reverse engineering’ our pitch and proposals to match ‘what they want to buy and how they want to buy it’.

6 - Start With Small

Let’s prove to one another we can execute a small deal before attempting a large one.

Given the potential for big data and AI to be across all aspects of the business we risked the scope of our work ballooning and with that came additional stakeholders (decision makers, economic buyers, users, beneficiaries etc), complexities and delays.

Finding and closing a small deal enables you to go through the legal, risk and procurement process. You get to discover how well the customer behaves during negotiations, deal close, engagement and how well they meet their obligations of supporting you internally and paying you on time.

Once the first deal is through and you are now ‘an insider’ or ‘a small incumbent’ it’s much easier to explore and close larger deals. Additionally as you now have first-hand experience of how your client behaves giving you a number of new levers to pull in your deal structuring, negotiation and close.

7 - De-Risk

Every time you interact with someone you are either boosting or bruising their ego and reputation. This includes when you are asking them to be your sponsor, buy something from you, use your product, provide a testimonial etc.

It’s our job, as founders and business leaders to think how we can de-risk all aspects of our engagement for our client. We want our customers to end up with pride, satisfaction, recognition and rewards for having been involved with us, not the opposite.

So our approach was always not to be transparent about the risks involved in any project or engagement, but we made it our business to be the ones that did the thinking and brought it to their attention first with a mitigation plan.

There are many things to de-risk for your client during the sales process:

  • What happens if your business goes under?
  • What if the technology does not work as expected?
  • What if our users don’t like the product?
  • What if something better comes out 12 months from now?
  • How can I get out of this contract if it’s not working for me?
  • What will my boss and colleagues think of me for having made this decision to buy from you?
  • How do we ensure Data Security, Data Privacy?
  • How will you support growth in my business?

8 - Bare Your Heart & Soul

As a founder, one advantage and differentiator you have over other 'sales people' from larger established businesses is being able to authentically represent you, your brand, your values and your company.

I vividly remember my first meeting with the Head of Big Data at Telstra in the early day of Contexti. He had reluctantly agreed to meet.

He was reluctant because he had a massive mandate at Telstra and was being courted by the ‘big end of town’ and couldn’t possibly imagine how this ‘little startup’ was going to be able to solve any of his problems.

He agreed to meet because wherever he turned, Contexti was top of mind (Own The Category, Be A Media Engine) and many were talking about us (Be Found).

One of my strategies for our prospect meetings was to first present a one page slide talking about our Values.

Here I would share how Contexti was going to be my ‘come-back story’ from a past failed venture and how these ‘values’ were not just words on a page but were the foundations I was betting my personal success and therefore the company’s success.

As I moved to the next slide to talk about the ‘problem space’ then pitch our 'solution', I was asked by the Head of Data to stop and go back to the Values page.

We spent the next half an hour talking about leadership, communication and a culture of risk taking and how we had both learned from our past experiences.

We went on to successfully sell into Telstra then secured Telstra as a sponsor of our Big Data Centre of Excellence.

Of course we brought them value but baring my heart and soul in the first meeting where I shared my failures and vulnerabilities was an advantage, not a disadvantage.

9 - Nurture, Don’t Follow Up

Whatever stage of the buyer's journey your prospect is at, you should nurture your relationship by continuing to be the ‘trusted advisor and customer advocate’, not the annoying person who keeps ‘following up’.

If a prospect:

  • truly has a pain or need,
  • sees your solution as compelling,
  • regards you as credible,
  • aligns to your proposal (priority, terms, pricing)
  • rates the engagement with you as low risk or even better advantageous for their personal and company brand.

Then they will buy when they are ready.

In the meantime calling to see ‘if they’ve made a decision’ does more damage than good. It makes you look desperate, needy and misaligned to their needs, priority and timing.

If you are not closing deals it’s not because you have not followed up and annoyed your prospect, it’s because there is misalignment in one of the criteria listed above.

Instead of following up, our goal should be to continue nurturing our relationships by adding value to them usually through premium content (educational, inspirational, insightful) and through making new introductions and connections to people and companies that will help them in their pursuits.

10 - Do The Work For Your Partners

Most tech product or service businesses will have partnerships with one or more of the large technology companies (Amazon Web Services, Google, Microsoft, Salesforce, Cisco, Dell, etc)

While all these companies have structured partner programs with dedicated Partner Managers and events from time to time, it is more likely than not that you are not on their radar because you would not be moving the revenue needle for them at this stage.

For example, time and focus would be better spent by AWS on their Accenture partnership than on Contexti.

Once you appreciate this then you will acknowledge that to get the most out of these partnerships or to push the potential like we did, it’s on you to do the groundwork for them.

At Contexti we generated love, attention and co-investments from our partnerships with Cisco, Telstra & AWS because we did the groundwork for them, demonstrating how we would benefit them and accordingly they went above and beyond to help us.

With Cisco and Telstra we launched the Contexti Big Data Centre of Excellence that aligned to their objectives of getting closer to the ‘developer and data science community’.

With AWS we jointly released a press release at AWS ReInvent in Las Vegas on the success of Seven West Media (Channel 7) lifting viewer engagement by 29% during the Rio Olympics with a solution designed & managed by Contexti hosted on AWS.

I know I said 10 but here's one more...

11 - Become A Media Engine

There are many benefits to becoming a media engine, including:

  • Create Value (personal, professional, company)
  • Grow Brand (known, liked, trusted)
  • Be top of mind
  • Grow email list
  • Grow social followers
  • Show product/service value
  • Nurture leads
  • Influence existing accounts

Right from the first day of Contexti we were disciplined and active with ‘creating noise’ but always with the guiding light of ‘creating value’ and as ‘customer advocates’.

Those who did not know us assumed we were a large US firm operating in Australia because of our brand positioning and volume of content we put out. Those who knew us always reminded me how we were always in their LinkedIN feeds.

Now What?

  1. Use this list of 10 Sales Strategies to consider how you can accelerate your Go-To-Market

  2. If you enjoyed this article share it with another founder

  3. Subscribe to The GrowthQ Podcast for more insights on how tech founders are building high-growth businesses.

  4. Want to explore how you can accelerate your Go-To-Market ? then let’s setup a call

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