skip to Main Content
What It’s Really Like To Pitch To VCs At Dreampitch

What it’s really like to pitch to VCs at Dreampitch

What’s Dreampitch?

Salesforce started a pitch competition a few years ago at Dreamforce, and has started extending this contest to regional World Tour events around the world.

I just wrapped up my pitch, and want to tell the story of how it all came together, how it felt to pitch a panel of highly-respected business leaders and VCs, and what lessons I took away from the experience after we lost.

The application process
A few months ago, Salesforce announced they would be accepting applications for the first ever Dreampitch in Toronto. Having worked in the Salesforce community for almost 10 years, I immediately put the application on my to-do list. As Lane Four’s lead consultant, actually finishing the application was hard, so with only 6 hours before the deadline, we got to work.

The good news is that we’ve developed enough marketing collateral though the Launch of the Lane Four application, so that part of the application was fairly easy. We submitted a two-minute demo video, some vision statements and, with the help of my wife, a two-minute pitch. I got the application in with 1 hour to spare. My wife and I then went for dinner, and almost forgot about the application.

Round 2
Eventually, the window where we expected to hear back passed, so I figured 3 qualified candidates had moved forward. But late on a Thursday, I got an email saying we needed meet with the Salesforce Ventures legal team the next day.

I was surprised that round 2 was remarkably simple. Then, I got the email saying we were in! We work with dozens of well-known startups in San Francisco and Toronto, but we work in relative back-office anonymity, so I was excited by this chance to tell our story.

The deck – Round 1
I’ve always taken sales decks very seriously. Together with Rebecca Rodrigues, one of our consultants and a talented illustrator, we got to work breaking down Salesforce’s suggested outline, the judging criteria and how to visually tell our story.


Actual sketched outline

It felt like we worked full-time on the deck leading up to our first mandatory pitch coaching session.

The deck – Round 2
As a self-funded, bootstrapped company, we had never created a pitch deck, so I was looking forward to a run-through with someone who sees these decks all the time. Let’s just say the session did not go well. The feedback was that we weren’t communicating our purpose, the problem we were solving, if the team were consultants or product people, and so on.

After reflecting on this feedback, I agreed, and we went back to work. We spent another week on this one, and I enlisted the help of my sales ops friends who have helped create investor decks to hear my pitch. This time the messages, what we did, the product, were explained much more clearly, so we locked in and submitted our deck.

Day before the pitch
Finally, the festivities were starting. We got a preview of the keynote hall, and with typical Salesforce flare the room was amazing.

The keynote team have a rock-solid scheduled and we needed to stick to it, so we waited our turn to do the walk-through. While we were waiting, I remember sitting in the keynote hall thinking of the 9 Dreamforce conferences and countless Cloudforce and World Tours I’d attended. This was finally my chance to get truly involved. I held the mixture of excitement and nerves for a while, then finished the walk-through.

Salesforce was nice enough to invite us to several events throughout the two days, so I hustled to get to the second half of the customer innovation talk being given by Tiffani Bova. Tiffani was making the argument to include customer engagement metrics on top of traditional sales and marketing goals. The potentially contradictory metrics around customer engagement and scale is something that would confront me the next day during my pitch’s Q&A.

The day of the pitch
The best part of Dreamforce and the World Tours is the ability to connect with former colleagues, friends and clients, all of whom wished me luck. At 2 p.m. I pulled myself out of the family reunion to take a quick conference call with a client; despite the pitch, work doesn’t stop. I ran through the pitch a few more times, trying to remember the points that resonated most.

Finally all the teams met up and went to the green room. With so much energy going into 10 minutes of onstage time, I kept fairly quiet. For me this was like my high-school swimming days, and I felt like I was prepping for a 50m sprint final. I needed to put everything I had into the time I had.

I had gone through the pitch so many times, I could do it without the slides. So I tried to focus on talking slowly and emphasizing key points. The actual pitch felt like I was on autopilot.  The five-minute pitch was my chance to show off what we’d done, now I was having fun. Afterwards, the stress of the day was over, which was a relief.

I’m so happy with the final slides, you can check them out here:


We’ve all been this person!

The Q&A
I was most worried about the Q&A, since it was the most unpredictable part. I did as much prep as I could, but nothing is like the real thing. Here I felt I was good, not great—and I needed to be great. The judges seemed to focus on a few things.

  1. How we could scale this idea, when I mentioned it took some amount of services to deliver the product
  2. What our competitive advantage was
  3. Why we’re the ones who could solve this problem

These were all questions I had prepped for, but I wasn’t quite ready for the feeling that these were coming from a place of skepticism. Maybe I’m reading into that, but it’s how I felt, and I kind of rushed some answers. You can’t prep for the emotion of the moment.

After giving my answers, I felt they were a bit flat. These were:

  1. How do you scale: I stressed that we didn’t need 2,500 customers, as our revenue per customer is fairly high, and that with only a team of 7 we actively manage almost 75 customers and clients. So that’s scale, right?
  2. What’s our competitive advantage: We’ve been doing this for 10 years.
  3. Why us: We’ve been doing this for almost 10 years and the people we work with keep coming back.

Not only did I use the same answer twice, I left out some powerful points:

  • Not only have we done this for 10 years, we’re uniquely qualified in modern sales organizations, as our 50 clients have raised over $500 million in venture funding, with multiple becoming public, and one major exit. You can’t find a company who’s worked inside the operations of high growth companies like we have.
  • Growth: This year we’ll do 40% year-over-year growth, with 500% growth from our first year in 2014.
  • I didn’t quite get the vision across. Yes, we have this lead routing tool, but through our experience in end-to-end revenue operations, we see Lane Four being the operational layer to managing the full sales cycle, from lead, to demo, to opportunity to renewal. The Lane Four platform will bring this all together and we’re going to be the trusted advisor to make it all work. Now that feels like a big vision.

The judges can only evaluate what they heard, so who knows if this would have made a difference. I feel they made a great choice with FunnelCake.

On not winning
This contest had no second or third place prize, exposure and articles like this are all we get. I do congratulate Marko over at FunnelCake, and throughout the day I was telling people that the experience was all I needed.  The reality is, I really wanted to win!


Not me holding a giant check

Later that night, I remembered the words of Tiffani Bova, who argued so passionately the evening before about customer engagement. This is the part I feel we aced: Half of our customers come from people who changed companies and want to work with us again. I use this stat in our sales decks, and it’s one of the most rewarding parts of what we do.

However, this style of organic growth and customer connection doesn’t exactly “scale” in the VC sense of the word. We’d created a stable, growing company, have a great team, and our customers really like us. We were also the only finalist with an app listed on the Salesforce Appexchange, presenting at a Salesforce pitch competition.

To not be recognized for all of this was difficult to take! I’m told I take rejection personally, and this was no different. But in the end, I felt we did enough to win, and that’s what matters to me.

What’s next for Lane Four
The good news is we have an active and thriving consulting practice, subscription customers starting to renew, and a strong pipeline. Even without the investment money, we’ll keep moving forward with our plans.

In the coming months, we plan to grow an SDR team to drive the product past word-of-mouth growth and to share our story. We’re going to keep adding to our consulting practice, as this drives revenue and is our key competitive advantage against our main competitor.

Now that the pitch is over, I’ve thought about the feedback from the judges and know we need to get a clearer growth plan, metricized goals for where we’re going, and communicate our vision a bit better.

After the pitch I’m even more excited for what’s in store and want to thank all the people who sat through my pitch to give feedback, Rebecca for a visually stunning deck, Salesforce for the opportunity, and the judges for giving our ops tool an open mind and seeing the problem is solved.

Back To Top