• Signing the largest deal in company history
  • Cross-team collaboration to understand customer stories
  • Inspiring the Sales Development to pick-up the phone

When I joined the company, they had just doubled the price of the platform to $120,000 annually. Dovetailing with this increase in price was the desire of leadership to go “upmarket” with more of an Enterprise sale.

During my time with the company I closed the largest deal in company history ($240,000) along with bringing in a variety of other notable clients. Additionally, I helped make the sale more strategic to justify the higher price-point, by developing a repository of customer stories, and advocated for outbound prospecting to incorporate the use of phones as a method of outreach.

Largest deal in company history


The story behind what it took to sign Rainforest’s largest deal ever.

The lead was sourced through an outbound email to the VP of Engineering. As is classic in a well-run organization, he forwarded the email to his brand-new Director of QA. Because she was new to the company and came from an almost two-decade career of automated testing background, this Director was less than enthusiastic to jump on a sales call.

The initial response from her was to ask for some information via email. Then the response was “can you come to our office and demo the product for us?” Not knowing what she wanted to see and not knowing who “us” was, I made the reasonable request, that we jump on a quick call before I do an onsite meeting. This changed the entire sales cycle.

The initial discovery call allowed me to understand a bit about the company, where she stood inside the organization and what was important in her new role as Director of QA. This was a company that sold very expensive software to very large companies and those companies demanded that the product work brilliantly all the time. Quality was crucial to their success. Moreover, this Director was chartered with improving the product, the speed to delivery and making the development team happy with QA.

With so many new pieces at this customer, from company strategy to organization’s structural changes, I still felt unprepared for a face-to-face meeting. Therefore, I asked for a second call to ensure that I was “most prepared for our custom demo.” The Director of QA obliged.


After we had the two discovery calls and I had started to build a relationship with my prospect (including texting with her), it was now time to meet in person and present our solution. When I arrived at our meeting, as is so common in sales, a curveball was tossed in my direction: I’d be meeting with not just the Director of QA, but then entire QA team and the VP of Engineering. Knowing that sales meetings with multiple people can go sideways quickly, I made a decision based on my experience: get everyone's contact information so that I could develop 1:1 dialogue after the meeting.

About 10 minutes into my custom-built demo, the VP of Engineering walked in and presumed to sit next to me at the long conference table. Not wanting to lose the thread off my presentation, I continued with the presentation and gently asked him to sign my attendance book---he smiled like he knew this was a real sales meeting and proceeded to put his contact info down.

As the meeting moved toward a close, it was clear that most of the audience (those individual contributors) wanted to stick with what they knew--automated testing--and were not thrilled about using our platform. The Director of QA, said “it’s an interesting product” and we’ll have to speak internally. More specifically, they had concerns around the price of the product being $240,000.

As the days followed and I began to build a deep relationship with both the Director of QA and the VP of Engineering, the price became less of an obstacle. This was because the alternative--which I had discovered through our first discovery meetings--was to hire between two-to-four more QA engineers. Knowing that that was the alternative and knowing how much testing we could provide them, the usage and the price were appropriate for their needs.

Once we moved to the contract phase, I  introduced myself to the CFO and their legal counsel. Over the course of three weeks, I quarterbacked the communication between our counsel and theirs, thus keeping the momentum going in a positive direction.

In the end, I brought in not only the largest deal in company history, but also the most successful customer for this Series A startup. The Director of QA has written blog posts about how she uses Rainforest and speaks regularly at Rainforest customer events.

From the initial interaction I think it’s critical to understand what the customer’s business is focused on, why it’s important to the individual and then only when you as the sales professional are fully prepared, discuss how your solution might be able to solve their problem or take their business to the next level.



Stories are the best way to communicate with people. Think about it, the most memorable learnings you have are probably from a story that someone told you. Whether it was your grandparents describing family history or a wonderful teacher in school breaking down a complex subject to a form that was easily understood, stories have a visceral impact. That’s why, with the world today where we are drowning in information, stories are paramount for good sales teams.

After a few months at Rainforest I realized that the team didn’t have a good repository of stories to relay to the prospective customers. Yes, there were stories floating around from rep to rep, but there was no easy way for new reps like myself to understand quickly the impact that the solution was making on our customer's business.

From my experience at Yammer I understood first-hand how impactful the telling of a good story could be for the business. Beyond the dynamic and entertaining stories that Yammer had on our website, our CSM team curated a whole host of other anecdotal stories from the customers they worked with. For example, one large global customer had multiple teams collaborating on a project in different timezones. Before Yammer, the response time needed to get an answer through email was at least 24hrs. With Yammer, someone could post a question and anyone on any team who knew the answer could respond. This cut the response time down to less than six hours.

Being a scrappy Series A startup, I quickly realized that the Rainforest sales team needed those resources and I decided to take action to help fill the void. Reaching out to my colleagues on the CSM team to ask for assistance, I found an enthusiastic participant: one of our brilliant summer interns.

With some hard work and hustle, this awesome intern was able to set up 10 customer meetings to discuss how they used Rainforest. Then, with some guidance from myself (at 19 she had never participated in a customer call before), she jumped on the phone and learned why customers bought the service, and what impact it had on their business.

At the end of her internship, she presented to the sales team the findings that had been truncated into a referenceable repository. It was terrific teamwork in identifying a void in the armory of the team and filling it quickly for others to use and follow.


The third area that impacted the Rainforest team was the use of the phone. When I joined the company, all outbound prospecting activity was through email. Nobody picked up the phone, period. Having seen this situation before and understanding quickly that the solution involved selling at the VP/CTO level I suggested that we add phone to the mix of activities for the Sales Development Team (SDR). After some time had passed and material conversations had commenced, the SDR manager started to advocate phone calls for the outbound strategy. The results were outstanding.