Travis Bryant: Building “oDeal”
Inspectable events as a blueprint for healthy sales & successful customers
Editor’s Note, October 2023:
I had the good fortune of sitting down with a friend and former teammate, Travis Bryant, to discuss the “oDeal” concept he introduced as SVP of Global Sales at Optimizely. With the current macro-economic crunch softening revenue growth across the software world, I thought it’d be an opportune time to revisit the concepts Travis introduced at Optimizely in 2015 to elevate the rigor, predictability, and objectivity we used in closing deals, growing revenue, and creating successful customers. Travis is a mechanical thinker, an empath, and a pleasure to learn from. He actively consults early-stage founders moving away from founder-led sales toward predictable, high-performing sales/revenue teams. I learned (& re-learned) a lot from this conversation and hope you do too.
[Reed Foster]: Mr Bryant, thank you for joining.
[Travis Bryant]: Mr. Foster, it's a real pleasure.
[RF]: Let’s get right into it. What are we talking about today and why?
[TB]: We had the good fortune of working together at Optimizely, where you may recall a number of sales concepts passed down to you like stone tablets. The one that perhaps was the most useful, or at least most intriguing, was this framework that we called the ideal Optimizely deal, or “oDeal” for short.
oDeal was built off a concept that I had learned from one of my mentors, Mark Roberge. He was salesperson number one at HubSpot, all the way to CRO through their IPO. He then wrote a book about his experience at Hubspot called “The Sales Acceleration Formula” and, in addition to founding a venture fund, he teaches sales as an adjunct professor at Harvard Business School. It warms my heart that the discipline of sales is being academically respected akin to engineering or finance.
Today we’re talking about where oDeal came from, why we built it at Optimizely, and how we operationalized it to inject rigor, discipline and predictability into growing our sales engine.
With the benefit of hindsight, we’re offering a few reflections on how early-stage founders and sales leaders might build something similar to grow their respective businesses.
When I first learned about oDeal, I thought it brought a notable operational horsepower, and objectivity, to a craft that is often muddied by human subjectivity. I remember it had a positive impact on both revenue and culture within the Optimizely sales organization, and those memories excite me to talk about it with you today.
Part 1: The Inspiration for oDeal: a Missed Forecast
Take us back in time. What was happening within Optimizely at the time you first birthed oDeal? Where did the initial inspiration come from?
It will be helpful to tell the story of how I stumbled into it.
oDeal was born out of necessity and, frankly, and also fear of getting fired. I airballed a forecast and thought I was going to get fired.
I asked a mentor for some help and he turned me onto the concept. So I'll tell that story as I think it nicely frames the why behind all this.
We had a great year in 2013, growing from $7M ARR to $21M ARR. A pretty awesome year-over-year triple. We’re squarely on the triple-triple-double-double-double SaaS growth wave and feeling really good about the upcoming year. Riding excitement from 2013, we took our eye off the ball and we just absolutely whiffed in Q1 of 2014. I had given our CEO a forecast of $1.9M - $2.3M in new bookings, which already had a wide margin of error. We ended up coming in at $1.4M. It was a pretty big whiff.
Optimizely was my first rodeo as a sales leader. It was on me to surround myself with mentors and advisors outside the company. I had been lucky enough to meet Mark Roberge through a friend. I called Mark and explained what happened, that it was clear we needed to grow up as a sales organization, that we did not have a lot of science in our sales process, and that I was keen to learn from him what worked while scaling Hubspot. Mark is a special guy, he’s not like most other sales leaders. He was a mechanical engineering major. He ran statistical regressions on interview scores correlated with quota attainment to figure out what questions to ask reps as a leading indicator of success. It’s next-level stuff.
The first question I asked Mark was:
“how do you inject more rigor into sales forecasting?”
But that question focused on the symptom (forecasting). The upstream root cause was a lack of rigor with which one guides a buyer through a buying process. So the question to Mark expanded to “how do you know, not through relationship or feel, but through objectivity, how likely the deal is to get done, and get done on time?”
Mark then talked me through this concept of injecting “inspectable events” into the buying process. Inspectable events are moments that happen between buyer and seller that can be measured. They’re objective. They either happened, didn’t happen, or haven’t happened yet. There's no debate about these events. They’re binary. And, importantly, the events are not what the sales rep does. They describe what the buyer does.
An example of the difference between a seller inspectable event versus a buyer inspectable event: “did we do a (product) demo for the customer?” You can measure whether or not that happened, but that doesn't tell you how the demo went. How did that demo go? How was it received by the buyer? Did the demo actually lead to more energy being created in the buying process? The better inspectable event in this example is “at the end of that demo, did the key contact within the buyer org widen access to their organization? Did they loop more folks in?” That's a measurable event the buyer either did or did not do. And this buyer behavior is correlated with a positive outcome in the buying process. Because no organization buys alone.
So Mark talked me through inspectable events, the difference between buyer and seller events, and what makes something an effective inspectable event. He then said “I don’t know what yours are. I know what mine are at Hubspot. You need to go figure out what the specific inspectable events are for Optimizely.” This was the launch of a process for me to figure out the key moments that happened in the Optimizely buyer’s journey, and how we could measure those with rigor.
When you heard about the concept of inspectable events from Mark, what was your first reaction to the concept at the time? How well did you think the concept might work at Optimizely?
I had two initial reactions.
My first reaction was: “this is so simple and obvious”. I was frankly annoyed with myself that I hadn't thought about the idea already. But when you’re in the storm of a startup you're constantly just trying to tip your head back in the water so your nose stays above the surface. I never really had a moment to step back and consider the operational sales infrastructure that needed to be built to keep adding more fuel to the fire. So I had an initial moment of “yeah of course this is something that we should have.”
My second reaction was: “what’s the best way to figure out what Optimizely’s most impactful inspectable events are?” We only had five or six sales reps, and call recording software wasn’t yet a thing. So I thought if I met with every sales rep 1v1 and asked them to walk me through their favorite deal they’ve done at Optimizely, I’d find out a lot. I treated this as an internal set of discovery sessions with the team.
“Take me through your favorite deal” was the only question that I asked the reps. The word favorite was important because I was interested in the deal they had the strongest memories about and the most fidelity of everything that had happened. I didn't care whether it was the biggest deal, the most competitive, or the easiest, I just wanted an instant reaction with lots of detail. The reps told me every detail, no matter how trivial. I sat there and wrote everything down.
I started to see common patterns emerge across the stories. This helped me form my first hypothesis of what the key inspectable moments were in our (Optimizely-specific) buying process.
In 2014, despite the Q1 miss, you still tripled the business from $7M to $21M in 2013. So the business was doing well. Did you have any hypotheses about what was going wrong in the sales process and/or any predictions about how oDeal would help?
Our lead funnel was strong. It wasn’t quite like shooting fish in a barrel, but leads were flooding in. There was a high-velocity spigot of interest in our product and company.
I remember managing that spigot as my first job out of college. It did feel like shooting fish in a barrel. It was fun to see so much inbound interest.
It was the land of milk and honey. I had reps, in their first quota-carrying role closing over $3M against a $2.4M annual target.
But I knew the fish-in-the-barrel moment in time would eventually pass. We tripled from $7M to $21M without sales discipline because we were in the right place, right time, right market.
If you're a student of SaaS companies, you know that there are these moments of dislocation that SaaS companies have to climb over, whether it's introducing a second product, evolving from product to suite, or moving upmarket to the enterprise. These are moments where a company has to grow up.
The grow-up moment for me was in Q1 of 2014. It was a wake-up call. I said to myself “if you don't apply some rigor to how you're managing the organization, someone else will.” The Q1 whiff was a wake-up call that we were flying by the seat of our pants a little too much.
Part 2: Building oDeal at Optimizely
Was there a sales process or blueprint in place at Optimizely before you began creating oDeal?
Early on, I noticed the very first thing reps were doing on calls was demoing the product. Coming from Salesforce, every sales engineer has a tattoo that says “no demo without discovery”. When I arrived at Optimizely and saw reps demoing early, my first reaction was “what are you doing, we need to stop doing that immediately.”
But the more time I spent shadowing reps, the more I realized what they were stumbling into: the Optimizely product works on any public website. Sales reps could go to any public website before a demo, and in 30 seconds, they could figure out how the business makes money, and what role the website plays in helping the business make money. Reps would then take the website, load it into the Optimizely editor, and they’d then have a custom demo ready for the prospect. Reps were basically using the Optimizely product as a trojan horse for thoughtful discovery on how A/B testing could help the prospect’s business. They’d load the website into the editor, create an experiment, and click Start. This was of course all for visualization purposes, we weren’t actually changing their live website. But we’d show them how easy it was to begin running experiments with Optimizely, and we’d use this to ask questions about their business goals to see if they were legitimately interested in buying. This behavior was something happening organically, before oDeal, which we then codified as an inspectable event in oDeal.
The wisdom in enterprise software sales is that you don’t want to demo too early. No discovery, no demo. Here, you were actually codifying demoing earlier than expected in a typical enterprise sales cycle. Were there any negative consequences of demoing too early in the sales process that you were observing?
Not really. Occasionally we would miss the mark if we were demoing tactical product features to someone who didn’t want to see that level of detail. On the other hand, it was such a visual product that people’s eyes would get as big as saucers. It was an emotionally powerful moment.
When you started interviewing your six sales reps about their favorite deals in search of patterns, what were some of the patterns you found?
One pattern that became obvious was that we did well [in closing deals and producing happy customers] when the prospect already had an A/B testing religion that had been adopted inside their organization. If they were already running experiments, they were likely using first-generation tools like Google Website Optimizer and Omniture SiteCatalyst (now Adobe). The difficulty of using these first-generation tools was the whole reason Optimizely was born.
An important note: when one documents a set of inspectable events, one creates a laboratory-created deal. We all know reality rarely matches a perfect and clean concept. We weren’t expecting each deal to follow every inspectable event. The goal of the inspectable events, if not to see 100% of them completed, is to hold up a blueprint against live deals, see where the gaps are, and have a productive conversation about how to move forward. It was a tool for analysis and action, not a pure science. Perfect science is not how lived reality works, at least not in enterprise selling.
Reality is nuanced.
That’s right. But what we did have, as a rubric for inspecting reality, was the ideal of a deal. It is the ideal Optimizely deal, hence the name “oDeal”.
Part 3: The Four “Fits”
How many different inspectable events were there in oDeal and how were these events categorized?
20-25 unique events, and they fell nicely into four categories, or what we called “fits”. Four fits.
The first was “Business Fit”. Business Fit is the “why bother” for the business, the analytical element, and the ROI model. “What’s the business case to make money or save money by using Optimizely?” Early in my career I thought:
“if we just have a clear ROI model, the buyer will of course be onboard, we can send the fax right over.”
I think we all know, with some experience, people make decisions more emotionally, with their gut, and then they back up their gut with data later. Deals involve more irrationality and emotion than purely acting on the projections of an ROI model.
That led us to our second category: “Emotional Fit”. Emotional fit is the strength of the human-to-human relationship between buyer and seller. A natural question here is how to insert objectivity and measure into something qualitative and subjective like the strength of a human relationship. Emotional Fit is like dating…you can’t turn it into a perfect algorithm. With a bit of creativity, you can add some objective measures to help judge the emotional connection.
My favorite inspectable event that we had in Emotional Fit was “are you in the text zone with your buyer?”
Think about the people that you text with, versus email or phone: it’s a different level of communication intimacy. Texting doesn’t win or lose a deal, but it’s certainly a sign of a tighter relationship between buyer and seller.
Inspectable events were also not just documented with the hope that they were executed, they were also the basis for our training and enablement of the team. With the previous example, we had a rep who confidently coached the team on how to begin a [professional and productive] texting relationship with buyers to win deals.
At the risk of giving away his or her trade secrets, how does one effectively enter the text zone with a buyer?
This rep said to the buyer, at the end of every first call, “I’m your key point of contact and I will be available, day or night, to help you in the evaluation. Let me send you a text so you have my phone stored in case you need anything. That will be the fastest way to reach me.” Buyers happily did so if it meant a better buying experience.
So far we have “Business Fit” and “Emotional Fit”. What are the other two fit categories?
The third was “Technical Fit”. Technical fit was our ability to evaluate quickly if we were going to play nicely with their existing technology. Perhaps we even had the advantage of a pre-built integration to a solution they were already using. We built a technical assessment to validate that we could and were going to do the things we said technically we could do. The Technical Fit was largely owned by our Solutions team, which helped drive adoption and accountability.
The last fit, and arguably most important fit, was “Readiness Fit”. Readiness Fit evaluated a prospect’s ability to be a good customer for Optimizely. We wanted to ensure they were as good for us as we were for them. We asked them if they had an existing A/B testing team in place, if they had a dedicated developer for the program, etc. We knew the presence of these things would make them a successful customer.
We’d also share these Readiness Fit events with the customer to best help them prepare to work with us. We weren’t yet asking them to commit to working with Optimizely. We were giving them ideas on how best to prepare themselves for the adoption of an A/B testing software and program.
I like how Readiness Fit is authentically framed through the lens of long-term customer success. “Hey, if you want to partner with us, here are the things you should be considering to optimize your long-term success, well beyond the point of just signing a contract with us.”
This is a tactical trap for young sales professionals and sales organizations when building and leveraging mutual action plans. A common mistake is making contract execution the last step in the plan. It’s the last step for you, it’s certainly not the last step for the customer.
oDeal was helpful in this vein in that it oriented our team’s mindset around long-term customer outcomes, and finding the right customers for Optimizely, versus just closing deals.
oDeal wasn't a mechanism to close more deals. oDeal was a mechanism to find more good customers.
That might be the hero banner quote of this conversation.
Part 4: Initial Rollout
How did you initially roll out oDeal? How did reps respond? How did your managers begin coaching with it?
In hindsight, a critical thing was to not present it as a finished product. It’s OK for it to lack polish upon initial rollout Especially with early-stage teammates and personalities who want to be part of building something and who embrace the sausage-making. I wanted to use that to our collective advantage as a team by ensuring there was a sense of collective ownership of oDeal.
Initially, we simply sat down with the team and said “we whiffed in Q1 and we need more rigor.” We appealed to everyone's mutual shared goal.
We then took the initial inspectable event ideas from the team based on their favorite deals, created the first version of the oDeal blueprint, and brought version 1 back to the team to see if it passed their sniff test. We then got teammates actively invested in making additions and modifications to the events.
Did you take a similar approach with managers too?
Yes. The first-line manager is the pivotal crux in whether or not oDeal gets adopted by a sales team. Because if they believe in it, then their day-to-day coaching, accountability, and support for their team are positively infused with oDeal events, fundamentals, and vernacular.
Were there initial naysayers?
There wasn’t outright resistance, but there was definitely an adoption curve. In the normal composition of a sales team, there are some free-wheeling artists who cherish the ability to be creative and do things their own way. The profession attracts folks like these. So the enterprise sales artist was a tricky persona to get on board with oDeal. For them, even if they’re not following the concept to the letter, ideally they’re injecting a bit of the underlying rigor and structure into their artistic instincts and outputs.
There were also teammates who were positive about the concept, but over time resorted back to their typical behavior. Human adult change is difficult. It’s difficult to pick up anything new.
Part 5: Seller vs. Buyer Behaviors
I want to return to a great example you gave to see if there are others. You mentioned earlier the nuance between a seller-inspectable event and a buyer-inspectable event. The example you gave was the difference between a seller merely giving a product demo and a buyer inviting more teammates from his/her organization into the sales cycle after a well-received demo. Are there other examples you remember that exemplify this important and subtle distinction?
ROI models. We did them. We could tie Optimizely squarely to how a business was going to make more money on its website. The problem with ROI models is that every salesperson at every software company has an ROI model.
I remember a prospect once half-joking:
“if I believed the ROI model from anyone who has ever tried to sell to me, I would have made more money than the GDP of most small countries.”
There’s a natural skepticism around ROI models.
So for oDeal, one of our inspectable events (in “Business Fit”) was not “did you build an ROI model” but “did the prospect sit down, review it with you, and did they add in their own ideas and revisions to the model”? It was a way to gauge if prospects bought into the model and were willing to stand behind it within their organization.
If you’re a new sales leader building out your own framework, you might instinctively skew your inspectable events toward seller behaviors. And it sounds like that might dilute the effectiveness of the events in moving deals forward.
It’s a good overall mantra to ask of each inspectable event: “is this something we (the sales team) are doing or something they (the buyer) are doing?” We want to measure what they, the buyer, do. That’s the thing that really matters in creating happy customers.
It seems that if you focus on buyer behaviors and outcomes, you may positively preserve the seller’s ability to be more of an independent artist because you’re not as prescriptive in how they approach their craft. Focusing on buyer behaviors focuses on outputs, not inputs.
That’s right. A good way to drive adoption of inspectable events internally is by framing them as a tool, not a religion. We’re not looking to create an assembly line of mindless workers stamping out widgets. We’re absolutely in favor of human ingenuity and authenticity in one’s own selling style and way of working. However, the seller's end result needs to foster these buyer behaviors. Because these buyer behaviors signal whether or not this deal is a good use of the company’s time.
That’s a really good way to look at it. You mentioned showing oDeal, or at least an external-facing version of it, to customers. What was their reaction? Did they enjoy being led through?
I think buyers appreciated it.
Anecdotally, there was perceived novelty around our process, which was a benefit because, right out of the gate, we didn’t end up looking like every other product-focused, transaction-focused sales team. It helped Optimizely stand out.
There’s nuance in how you position the methodology to buyers. We reminded the buyers we weren’t asking them to choose Optimizely by engaging in this process with us. We communicated this as the most efficient way to evaluate our software, which buyers appreciated because buying software isn’t their day job.
All sales organizations fight the stigma of sleazy, gimmicky, unproductive sales tactics. We all know the stories out there, and the stigma exists because of these stories. Even with the optimal communication of oDeal, we were met with an occasional skeptic who was cynically convinced that we were just trying to trick them into buying something. There will always be skeptics to address. But even the infrequent skeptic usually came to appreciate the efficient process, and I think that helped us chip away at their scar tissue of poor prior sales experiences.
Part 6: oDeal in Forecasting & Culture
How did you use oDeal in forecasting, both within the sales organization and upwards with the Optimizely C-suite?
It was imperative that oDeal language made its way into every deal review, every pipeline review, and then every forecast call. This only happens through the consistent commitment of the leaders, the way they’re analyzing opportunities, and the way they’re communicating with their teams.
Tactically, for each inspectable event, we had checkboxes on the opportunity record in Salesforce. It was easy and became second nature to look at deals through the lens of these checkboxes during pipeline reviews and forecast calls.
Were they “Yes/No” checkboxes without any room for subjective input?
Yes, but we learned pretty quickly there’s a difference between “No, I didn’t do this yet” and “I did it, but the buyer did not engage.” We initially didn’t have visibility if an inspectable event was attempted but unsuccessful, or if it had simply not yet been attempted. We reimplemented oDeal in Salesforce when we experienced this important nuance. We added a default setting for the dropdowns in Salesforce of “Not Done Yet” in addition to “Yes” and “No”.
We also made sure oDeal was simple and easy in the Salesforce mobile app. I was really trying to lower the barriers to entry and to keep the information clean and simple so we could effectively analyze opportunities. With a focus on simplicity, the message to the team was “I’m going to do everything in my power to make this as easy as I can, but then you need to do it and I’m going to hold you accountable to doing it.”
Part 7: Risks
Where did oDeal fall down? Or where does it run the risk of falling down?
The biggest risk is a last-mile execution risk. You can have a beautiful, elegant methodology, but the only way a methodology continuously works is through rigorous commitment and application in the tiny moments of every deal and every conversation in the business.
I touched on this briefly above: actualizing oDeal day-to-day by using the right vocabulary is key. The methodology is activated, or forgotten, in every moment-to-moment conversation amongst all teammates. Working to inject a vernacular into the collective organizational conversation can be potentially exhausting for a leader, especially in the beginning. It requires relentlessness.
There’s also another human behavior risk: people get naturally fired up to launch something. People get less fired up to maintain something. Fatigue can set in after the initial roll-out, and I remember that from the Optimizely days.
As a leader, you have to commit to it, and committing to it requires a rigorous energy to drive it through the organization because, if not, it’ll die in the last mile.
Closing: Reflection
Closing question: you now have the luxury of hindsight, at least for oDeal at Optimizely. If tomorrow you went to an early-stage software business or were giving advice to a founder or sales leader in an early-stage company, what advice would you give them about leveraging inspectable events? And how do you know a startup is even ready for its own flavor of inspectable events?
This is the nature of the work that I do today. I work with Series A startups that are transitioning from founder-led sales to building their first sales team. I don’t think it’s possible to implement something like oDeal too early in your company lifecycle. The earlier the better.
An early version doesn’t have to be a sophisticated McKinsey-esque production. I coach founders early on to have a sophisticated point of view on the characteristics of their ideal customers--a point of view beyond firmographic attributes like employee count, industry, and revenue. I coach them to understand their customers’ business headwinds and tailwinds, their character, their culture, and how they make decisions. With a deeper, authentic understanding of their customer, a founder or leader can then better understand the ideal buyer’s journey to lead these early customers through.
An early inspectable event framework doesn’t need four fit categories and 30 inspectable events. But it’s never too early to ask three key questions:
“How do we know we’re spending the right time with the right prospective customers?”
“For these ideal prospective customers, what does the ideal buyer’s journey look like?”
“In this ideal buyer’s journey, what are the ideal behaviors we want to guide the buyer toward?”
If early-stage startups can answer the above three questions with rigor, they can better position themselves to one day be category leaders with high-slope exit velocity. And they can avoid a lot of pain down the road.
Think of it as R&D for go-to-market. In the same way there’s a rigorous process for product teams to help them figure out what to build for customers, this is a similar mental muscle to help go-to-market teams figure out how to design the ideal buying experience for their ideal customer. If a startup is going to market, and is investing time, money, and effort into building its software product, why not protect that investment by taking a similarly rigorous approach when designing the sales experience you take your buyers through?
It’s customer experience as the product. Or customer experience as an experiential layer atop the software product being purchased.
Yes. It’s a critical experience layer on top of the product.
Thanks for your time and perspective.