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The Pitch Casino: How To Win When You Lose

Updated: Jun 25, 2021

Recently we invested time, energy and money into a new long term business opportunity, however, after 2 months of shortlisting and endless meetings we found out that we were unsuccessful in winning a long term contract. (miniature violins play).

Now, I am big enough to understand that sometimes the better person wins and you must be dignified in defeat. I have also worked in the corporate and agency world long enough to not be too disheartened when decisions don't go your way. Thankfully we have been on the winning team more often than not, so here are my takeaways to help you understand that there are no guarantees but you can still come out on top.

It's not you, it's me...

Take into account that there are usually multiple variables that are completely out of your control. A little like a casino where the house always wins. Most of the time you will never know the true reason as to why you were unsuccessful, however, here are some of the most common examples that I have come across over the years by doing a little post pitch digging.

  • It was a due diligence exercise (mandatory requirement to have 3 vendors) and you were never in the running

  • The business wanted a fresh set of ideas to ‘pivot’ their own strategy

  • They are now looking to manage this in house

  • Commercial cogs have already been greased with an incumbent

  • Leadership changes / internal conflict

  • Budget changes / internal conflict

  • Bad timing - external market forces; political, social, environmental factors

Sometimes when you are brought in as an external agency to work alongside existing in-house marketing/sales teams the CEO or VP loves the concept but simply questions the whole internal team, wondering 'why have we not been doing this already'. Then there is a big clear out and the project doesn't get off the ground.

Hell, a lot of VP’s of Marketing commission projects to see what ‘leading’ agencies would suggest, then inevitably claim that it was 95% their idea and bin the external commission altogether.

So when do you know whether to play and how much should you stake?

Follow these simple steps to make sure the odds are in your favour:

1. Validate the opportunity!!!!!!

Sales and marketers are good at setting unrealistic expectations and throwing ‘hot leads’ over the fence at the first sniff of commission or at a glimpse of achieving false KPI’s. It's your job to do your due diligence, do not accept low quality as it will kill time, energy and confidence with no outcome. Follow these tried and simple steps

  1. Understand who you are engaging with, is there a direct need, do they suffer from common pain points your service or proposition addresses, and is there a desire for change? (yes, move on…)

  2. Do they have the correct senior buy-in and authority to make this happen? (yes, move on). Ask who is in the wider sphere of influence? Are there any existing relationships you can leverage?

  3. Do they have the correct ballpark budget? (If not, don't waste your time)

  4. When do they want it, is this timescale feasible? Will it ever happen? (If yes move on)

  5. Culture - could there be a positive working relationship? Could there be personality clashes? Is expectation management going to be an issue? There will always be a challenging point in every supplier relationship however if you have built up ‘relationship brownie points’ along the journey then you are both more likely to want to find solutions rather than problems.

  6. Market / Business change - assess the landscape, do your research. What major changes could be on the horizon for this industry / company / individual

  7. Competitive environment - Who are you up against, who is the incumbent - know your enemy

Once the initial assessment is complete you have the power to make the call - do I stick, twist - will I bust?

The likelihood is you will progress into pitch mode as not many businesses can turn away lots of potential business, however, you have now identified any red flags so grade your opportunity and invest in the pitch at an appropriate level. Assess the budget, time and resources required to win, do the pro’s out way the cons?

2. Build relationships Once you do go ahead remember you are here to take your prospect on a journey to educate, delight and aim to present a compelling argument as to why you are the best solution to make it happen.

For AOD, we run a deep dive explanatory session with the prospect leadership team. This is not just to gain the correct level of information to create tailored recommendations but also to meet and influence the wider stakeholders. Relationship building is critical. Trust accounts for 65% of buying decision making, so go the extra mile.

3. Remove subjectivity

Opinions can be painful to manage especially when there are many stakeholders to try and blend together. You can not please everyone's taste, personality or requirements. Tailor your recommendations around credible facts, research and data. Run relevant primary and secondary research to reinforce decision making, remove the opportunity for vague interpretations and control the narrative.

Design a strong UX for the audience in the pitch. Who is involved, what is the journey you want to take them on. Design a storyboard for the pitch and follow that narrative throughout. Keep the energy high and your messaging short and sharp and value-driven.

4. Personalise & humanise

Make sure this hits home, tailor the content and use cases. Showcase the most relevant work to reassure the prospect that they are in safe hands and it's right for them.

Although this can be overworked use emotional messaging to trigger the response that progresses the narrative.

5. Be flexible

Build flexibility into the commercial terms, whether that is milestone payments or absorbing a shared risk % into the partnership, this is where the prospect will want to flex their muscle and feel there is a positive working relationship.

6. Take control

Don't let the opportunity dwindle. Plan the major project milestones and showcase the next steps to activate and implement the project. Do the thinking for the client, answer any doubts by addressing typical objections and don’t forget to encourage participation at key stages. If you have done your job correctly you will be able to anticipate the outcomes and respond with seamless confidence.

What if they are disengaged?

You can tailor your presentation to have breakpoints and different scenarios based on the feedback from the audience. If the narrative is strong (including both emotional and professional directives) be bold, call them out! Use this as a warm opportunity to re-engage.

6. Debrief and gain feedback

After the pitch, ensure you gain feedback. This will help you understand what worked, what didn't, you can take this forward and where possible improve.


Find out who won and why. It is fine to know that there are better companies, strategies and people out there. That's why you're in this business, this should motivate you to be better and continually invest in improving your delivery and proposition. Find out what they do and evaluate to see if this could be a future opportunity for you.

Take solace in the fact that:

  • The more you do the better you will get.

  • You will have improved your market and business insight and can potentially re-position this for a market competitor

  • More ammunition for creativity for future pitches; reuse and repurpose.

The Importance of strong sales alignment

In my experience, where we were supported by a high calibre sales team who truly presented and ‘hot lead’, we were successful in around 80% of pitches, if the sales team were not top of their game, this reduced to 20% hit rate.

Work closely with your sales team, understand their requirements to support the buying journey, do they need more content, proof, offers etc to improve the quality.

Gain feedback from them to understand objections and create process flows, content and even scripts to support them in overcoming hurdles and gaining maximum buy-in.

The typical b2b buying journey is between 3-12 months. Support the nurture and requirements and ensure you are working closely with them drive prospects through the sales funnel with appropriate mechanisms in place to recognise buying signals.

So what did I learn

Don't gamble! As you can see there are many factors that may mean you will not always win, however, if you do your homework, qualify the opportunity, invest at an appropriate level and set realistic conversion targets, then you shouldn't go too far wrong.

In this recent scenario for AOD we found that as an early-stage, growing business, you may have to accept lesser quality leads and work towards reduced conversion targets to begin with as the odds are slightly stacked against you.

Play the long game, build use cases and a breadth of audience-specific case studies that are tailored for your core verticles and audiences. Invest more client stories and potentially work in case studies into the initial agreement and commercially incentivise these if need be.

Good luck and may the odds be in your favour.

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