Anatomy of a perfect sales pitch: Examples and tips

Perfection isn’t spontaneous, it’s earned – especially in sales. 

At this year’s kickoff, we had an old fashioned pitch contest, incorporating the latest Outreach messaging and techniques. After all, what’s sales without a little competition… and some practice. 

At Outreach, we have some of the best talent on the planet. We’re constantly honing our skills selling to other salespeople. Plus, we live and breathe the platform we sell. That means Outreach sellers are equipped with both real-world experience and the best tech in the business to consistently smash their goals. So this competition was fierce, but one Outreacher was a stand out.

Mia Lilienthal took the stage and walked away as pitch competition champion. Typically, Kaia, Outreach’s conversation intelligence software, would record and analyze sales conversations. But since this was a stage competition, we’re analyzing her pitch the old-fashioned way to break down the best examples and tips for the ultimate sales pitch. 

We break down what made her pitch perfect, and we do mean perfect.

1. She went straight to the decision maker and broke the “rules” 

All our participants dazzled on stage. Truly. But Mia did one thing the others didn’t: she pitched to a real sales leader. Kevin Bognar is Outreach’s SVP of Sales and Kickoff’s emcee. When he left the stage to let Mia do her thing, she grabbed his attention and incorporated him into her pitch.

Kevin happens to be one of our key buyer personas, and practice makes perfect. This elevated Mia’s pitch with real life context while upping the stakes. But this was a real wild card: what if Kevin didn’t play along? What if it didn’t go well and Mia left a bad impression on a leader? Or the whole GTM organization in the audience? In the end, Mia won the competition, so her risk paid off. 

This is also a prime example of breaking a phantom rule. Phantom rules are the unwritten rules we unconsciously follow, they’re the habits and behaviors that shape unnecessary dogma. Breaking phantom rules isn’t about being rude or exploiting relationships — manners still matter. But there was no explicit rule that said you couldn’t bring-your-own-prospect, the other participants simply followed the expectation of standing on stage and pitching to the audience. Mia broke the phantom rule to take her pitch to the next level. 

2. She got straight to the point and demonstrated her knowledge of the market and her product, without regurgitating messaging

“So Kevin, tough market, yeah?” Mia didn’t waste time with small talk, but she didn’t jump straight into product talk either. Instead, she demonstrated interest in what Kevin was experiencing, instead of her interest: closing the sale. She’s still leading and maintaining control of the conversation without losing focus on the shared goal: to solve the problem our customers are facing. 

She accurately depicted the market and its challenges, while cleverly integrating Outreach messaging and slowly incorporating our offering. Kickoff was full of training and insights, and Mia wasted no time implementing that training. We can’t reveal all our secrets, so we won’t highlight exactly where they lie in Mia’s pitch. But that’s also what makes Mia’s pitch so perfect, it flowed organically, making the messaging feel real rather than marketing fodder. 

It’s a full 5 minutes before she begins product talk, but when her moment comes she doesn’t miss a beat and discusses both beautifully. 

3. She maintained control of the conversation while still addressing concerns 

Mia crushed the if’s and but’s before they happened, and she did it with style. She discussed typical solutions to the same market problems: more hiring, Frankenstacks, human shortcomings… shifting to what could be controlled and teeing up our product as the right solution. 

4. She multithreaded (even if only fictionally)

During her conversation, Mia cited other Outreach sales leaders Angela Garinger and Sheri Hedlund. We know that she didn’t actually do that since this was a fictional pitch, but she demonstrated an important skill: multithreading. In theory, she communicated meaningfully across the organization with multiple contacts. And good thing too: Outreach data indicates when more than one contact is engaged, deals are 37% more likely to close.

If we could give one piece of advice to Mia, we’d suggest going beyond the sales org. Even though they are her target audience, Mia could better her odds with cross departmental threading. Cross-department threading has the potential to increase win rates by 56%.

5. She establishes next steps before the conversation winds down

Mia flows through the conversation pretty effortlessly, but she doesn’t wait for the lull or thumb-twiddling to establish next steps. Mia is at the peak of her pitch when she mentions her preferred contacts by name and what they should do next. This makes it easier for the prospect to say yes, and easier for Mia to move the deal along and multithread even further. 

6. She used her strengths and ended the conversation graciously 

Mia wasn’t just a great salesperson, she was herself. From those of us that know her, this is Mia: friendly, informative, eloquent, and encouraging. She wasn’t trying to mimic the guile of the Wolf of Wall Street, or the prompt diligence of Dwight Schrute — she was leading the conversation the way Mia leads conversations. She let the conversation flow while implementing fresh Outreach training. She brought the conversation to a comfortable close where both parties were feeling optimistic and satisfied. 

The craziest part? Mia isn’t technically a salesperson. Mia is a CSM here at Outreach. Mia’s position does have plenty of sales elements, ensuring thorough integration of the product, expanding packages, and securing renewals. But Mia is proof that sales talent can come from anywhere, and she used her real experience to her advantage. Mia has unique knowledge of our product and what our customers love about it, and she implemented that into her pitch. She wasn’t thinking about what a salesperson would say, she thought about what she would say. She used her organic knowledge to her advantage. 

The perpetual pitch

Crafting the perfect pitch takes time and practice, and watching Mia’s pitch is a great place to start. 

Of course, we’d recommend Outreach. Kaia makes pitching a lot easier. Kaia is our conversational intelligence software, guiding and supporting sellers in real time. Kaia analyzes conversations as they’re happening, providing recommendations like product features, rebuttals to the competition, and objection handling. And it works: utilizing Kaia can using Kaia during a call moves deals 19% faster and boosts win rates by 41%. The platform also monitors sentiment and recommends next steps, recapping calls and guiding deals so you can do what you do best: sell. 

You can do these things without Outreach, it just takes more time. If you can, review your own call recordings to analyze your conversations and their wins and pitfalls to shape your pitch. 

The sales cycle never ends, nor will perfecting your pitch. As markets shift and your offering evolves, you’ll need to continuously evolve and practice — but that’s part of the challenge and the fun.