Roadmunk turns 5: The biggest challenges, surprising delights + hard knock lessons
Good things come in fives for Roadmunk. At the end of 2017, we celebrated our 5th anniversary. Our team had grown to 50 (and growing 🚀). Our customer base is over 1,500 (and growing). And that base is spread out across 5,000 cities worldwide.
I’ve experienced many delightful moments in the last five years as a co-founder and CEO — from meeting each new employee to escaping brutal Toronto winters together on two separate retreats in Costa Rica and Nicaragua.
I’ve also faced a lot of challenges and learned plenty of lessons along the way. So, I wanted to kick off our sixth year in business by sharing my story — an uncut version of this roller coaster ride. This is my experience as a founder, CEO and product manager at a growing startup — the hardest moments, happy surprises and most important lessons.
2013
What happened this year: This is the year that Tomas Benda and I founded Roadmunk. We worked out of my house for the first year — a prospect that Tomas didn’t mind because in his words, “Latif makes really, really good chicken.” I bbq’d a lot of chicken for us in that first year.
The hardest part: Laying startup idea #1 to rest
Our first year was tough because we realized — six months in — that our great idea had already been thought of by someone else.
Our initial plan was to build a requirements management platform for product managers. I spoke to ~80 PMs in our first six months to validate this idea. Only a handful of them were bought-in. And that’s because they had already adopted a requirements management platform into their workflow. Jama Software had built what we were envisioning — really well (I’m a big fan of them). There was no way we would have been able to catch up with them, so we decided the market wasn’t right for us.
We had to ditch months of work and start all over again.
While this realization was happening, I gave a presentation to ~30 PMs about the ecosystem of product management tools. It was an amalgamation of all the interviews I had done — plus my own experience as a PM. I had one slide about roadmapping. I spoke to how annoying it was to roadmap in Excel/PowerPoint, and I explained how one PM I interviewed built an internal tool just to create roadmaps. A guy to my left said, “I’d pay for that.”
Seed planted.
Creating and presenting roadmaps was a huge pain point for me as a product manager at Miovision. And it was a pain that came up in many of the requirements management interviews. Roadmapping software became a viable option to replace our now-dead requirements management idea. But we had limited funds left.
So, Tomas and I came up with a deadline. I would spend the next month validating the roadmapping idea and he would take on consulting work for a local startup to make some money. The pressure was on.
The most delightful: Validating idea #2 by signing customer #1
I took a different approach to validating our roadmapping idea. I built a landing page that described what our roadmapping tool would do and how it would benefit PMs. I ran an inexpensive SEO campaign that targeted keywords like “product roadmap” to get it in front of the right people.
Eighty people entered their email into that landing page because they wanted to learn more about our roadmapping platform. This wasn’t rock solid validation but it was enough to push us forward. And it gave us 80 new people to bounce ideas off.
And remember the “I’d pay for that” guy from my presentation? His name was Andre and he was a PM at P2P Communitech. I reached out to him to talk about his roadmapping woes. Together, we listed out what he would want from a roadmapping tool. I transformed those requirements into wireframes and designs for Roadmunk V1.
Andre signed on as our first pilot customer after seeing the wireframes and designs. That was all the validation we needed. And as a result, we were accepted into an incubator program.
The biggest lesson: Build a company that solves a problem you’ve personally experienced
I believe that the most successful founders are the ones that are building something that solves a problem they’re familiar with — a pain point they’ve experienced first-hand.
I spent over a year at Miovision struggling with roadmaps and aligning the executive team to my product strategy. Roadmunk solves a problem that caused a lot of stress for me as a PM. I knew the problem inside and out from the very beginning. And this shortened the validation process for our new idea.
My inside-out knowledge shaped how I spoke to PMs about our roadmapping idea. I already knew how Roadmunk would help them because their pain point was my pain point. For validation round two, I didn’t ask the same types of discovery questions that I did for requirements management — like, “What would your life be like with this tool?” or “On a scale of 1–10, how much easier would your life be with this software?” or “What would make you come back to this tool over and over again?”
I approached the validation interviews from the angle of, “Hey, I know this is a huge pain point for you and here’s why. How much is a solution worth to you?” (It also helped that the people we were talking to found our landing page on their own and gave us their contact info willingly.)
This second round of validation left us with something much more concrete. The people that signed up through our landing page agreed to be pilot customers and they were willing to pay us once the software was built.
Choosing to build a company around a problem you know will save you months (six, in my case) of chasing the wrong vision.
2014
What happened this year: We signed our very first customer before we even built the app — this led to us moving out of my house and into a coworking incubator space. And we built and shipped the first version of Roadmunk with the help of a couple engineering co-ops.
The hardest part: Shipping the product too soon
It took twelve months to build and ship Roadmunk to the public. I was in full product manager mode. My days were consumed by soliciting feedback from our pilot users, translating it into requirements, designing it, prioritizing it and then making sure quality was up to snuff once dev was done with it. Over and over and over again.
I knew the product wasn’t ready when it came time to ship. It wasn’t feature complete, but there was just enough in there to maybe start generating revenue. At the time, users could create a basic roadmap and move items around. The ability to collaborate wasn’t baked in yet, exporting was limited and the roadmap would get real precarious if you tried to add too many items.
Shipping a product that you’re not 100% confident in is a terrible place to be as a product manager. And, on top of that, I’m a type A personality. Perfectionism can be my kryptonite. At the time, I couldn’t reconcile having to ship an incomplete product.
But even though the product was missing a few key features, the ones we did have worked really well. PMs used the tool and engaged with it — this quelled my anxiety quite a bit.
Now I know that every product’s first few iterations are far from perfect — they’re often poorly designed, missing key features and super buggy. And a great PM is totally ok with this. The imperfection leaves plenty of room to make the product better based on user feedback. The sooner you ship, the sooner you can fix.
The most delightful: People started to pay us $$$
I wasn’t thrilled with the product that we shipped and I was anxious about how it would be perceived. But the landing page came through again. More people were finding it and signing up.
The delight in 2014 is pretty simple: We had 50 paying customers within 90 days.
I was extremely surprised and delighted when they started entering their credit card info into Roadmunk. Immediately.
I was dumbstruck. Tom was, too. We realized that we had something that was really special.
The biggest lesson: The Chasm is real
Quick refresher on the diagram below. It was created by Geoffrey Moore and published in his hugely influential book, Crossing the Chasm, about marketing technology products. Basically, the chasm outlines the different types of customers who will adopt your product at different stages of its life cycle.
It breaks down like this:
- Innovators: Tech enthusiasts who will always be the first to try new things.
- Early Adopters: Visionaries who are easily sold on new products. They are content with incremental improvements rather than perfection.
- Early Majority: Also known as “pragmatists.” This crucial section of the mainstream market requires a high level of quality and infrastructure to buy.
- Late Majority: Also known as “conservatives.” Their needs are similar to those of the Early Majority, but they’re more resistant to purchasing.
- Laggards: Late-to-the-party skeptics. This group rarely buys technology products.
In our first year of general availability, I learned to lean on the innovators/early adopters to use our product and provide feedback. Keep the early majority at bay for as long as you can. A year, at least. They will only want more features, workflows and uptime guarantees that you cannot give them. Trying to keep them happy will force you to make bad decisions early on that will be difficult to bounce back from.
We focused on building for 10% of our users in the first year — the innovators and early adopters. We set the expectation of “Hey, our product is not perfect. It can do this, but not this. The bugs might be frustrating, but we think you can help us make it better.” Sell the vision of the product and their contribution to making it happen.
They provided feedback that helped us build the right features at the right time — and we eventually got Roadmunk to a place that would make the early majority happy. And the percentage of customers we aimed to keep happy grew and grew as our product matured.
2015
What happened this year: Tom and I were still working out of the incubator co-working space. We began to meet with VCs to raise our seed round (we closed in November). And we started to grow our team by bringing on product, marketing and support hires.
The hardest part: Getting inside a VC’s head
Fundraising is never easy. Rejection sucks. And getting in front of the right VCs is tricky. But the hardest part for us was trying to figure out what the VCs were really thinking. And they didn’t answer our questions about their processes or what they wanted to see from us. We didn’t know how they made their decisions to invest or not.
I found this uncertainty particularly annoying (again, I’m — ahem — Type A), so we created our own rules of engagement for VCs, a structure with deadlines that they had to buy-in to.
My partner in fundraising is Jalil Asaria, our VP of Sales and Customer Success. First, we perfected our pitch. We had it down-pat after about 10–12 meetings. Next, we tackled the negotiation process. We created a timeline to get us from the pitch to the “Yes” in four weeks.
It wasn’t easy. It took us ~50 meetings to perfect that four week window — figuring out the right amount of meetings, when to take them to dinner, etc. We got a lot of “maybes” over those months and it was frustrating.
However, we managed to raise our seed round in November with an incredible Canadian VC fund called Golden Ventures.
The most delightful: We moved over half of our users from monthly to annual subscriptions
At the start of the year, 30% of our customers were paying upfront for an annual subscription. The 70% that were paying for a monthly subscription could easily cancel and move on at any point. This was scary given how much infrastructure work we had to do to improve and scale the product. We needed to buy ourselves some time. At this juncture, retention was more important than growth.
We ran an email campaign that incentivized users with a 30% discount if they upgraded from monthly to annual subscriptions. By the end of that quarter, we doubled the amount of customers paying us to use Roadmunk for the year.
This is delightful on many fronts for a founder. It gave us stronger negotiation leverage with our investors. We were able to hire more and grow faster. And, most importantly, I didn’t have to toss and turn at night worrying about payroll.
The biggest lesson: Teach your customer support team how to sell
Do not hire any sales reps this early on in your startup — before market-fit is solid or if ARR is less than $1M. Instead, teach your customer support team how to close transactional deals.
Jalil, our VP of Sales and Customer Success, decided to take this approach for a few different reasons:
1.) Good sales reps are expensive and they are sometimes one-dimensional. Your Customer Success team can often do a lot more — they can run demos, train users and answer all product-related questions throughout the user’s entire lifetime as a customer. This saves money on headcount AND provides a better experience for users because they don’t have to be bounced around from sales to support rep.
2.) A big sales team influences overall culture in a big way. They demand a lot from marketing and other teams within the organization. A sales-driven culture = pressure. A support team that can sell in a more organic way relieves a lot of that high-wire stress.
3.) It’s easier to win land-and-expand deals. Happy, well-trained users are the biggest advocates and sellers of our software. They’ll show their colleagues how to use the tool and explain why they should — and the support team plays a, well, supportive role in converting them to paid users.
2016
What happened this year: We moved into our first legit Toronto office space at the end of the year. And we got to know some awesome product managers from really cool companies because they signed up to use Roadmunk.
The hardest part: I made some product decisions that no one agreed with
We faced a lot of difficult product decisions in our second year of general availability. Some decisions led to the path of differentiation in the market. Others would have turned Roadmunk into a carbon copy of the competition (something I really, really wanted to avoid).
I spent a lot of 2016 in the middle of tough conversations with the team. I was constantly going against the majority. I wanted to invest more time in improving the parts of our product that delighted our users. Others wanted to reinvent entirely different parts of Roadmunk.
Our product manager at the time insisted on moving our most-requested feature to the top of the queue without fully understanding the impact it would have on our infrastructure. I had to intervene and push the feature out four to six months in order for our dev team to handle it.
From a co-founder perspective, situations like these are stressful. I had to prioritize employee happiness over end-user happiness — and being forced to choose between the two feels like being caught between a rock and a hard place.
I was basing my decisions on my own instincts — but that’s not the type of reasoning that sways pragmatic product people and developers to change their minds. I had to dig in and always backup my assumptions with market research and qualitative information (which takes up a lot of time).
The most delightful: Good vibes only in Costa Rica
2016 was a year of perpetual growth. The special kernel of an idea we landed on in 2013 had grown into a business that was growing 30–40% month-over-month.
Yeah, we had challenges around product prioritization — but (and please excuse how trite this is) the positive vibes felt around the office were potent.
And we shipped the whole company to Costa Rica for a month. This retreat solidified our mandate to be a culture-first company. For us, culture = balance. Career and fun. Hard work and freedom. Business and friendship.
You can read more about why I took the whole team to Costa Rica here.But the gist of it is: A team that knows each other grows together. And we’re still reaping the benefits of the core team being so in sync with each other after living and working together abroad for a month.
Plus: In Costa Rica, we surpassed several sales milestones and it was the strongest month we’d had up to that point.
The biggest lesson: Founders — don’t give up control of your product too soon
Up until early in 2017, I oversaw a lot of the decisions made by the product team. I truly believe that handing over your product to another PM is a mistake when done too soon.
I say this even though being so involved with product for so long took me away from working closely with other teams, like customer success or marketing. Being a product founder / CEO is a fine line to walk at times, which resulted in unpopular decisions and moments of friction.
There are plenty of small hiccups that have made this lesson evident for me.
For example, we were working on a revamp of our field management functionality. I decided to be completely hands-off on this. One of our very talented designers led the project without much oversight from the PM (I wasn’t aware of this particular puzzle piece). The release of the revamp kept getting pushed out further and further — and CS was getting anxious. Turns out, communication between the PM and engineering was too infrequent. I had to step in and make some decisive decisions to help ship it faster.
This mishap cost serious dev time.
Until recently, I I felt like I had to be tied to all of our big product decisions.
I wanted every single one of our PMs to think exactly like me because Roadmunk was built based on a pain point that I’m all too familiar with — and I think my instincts are often right when it comes to what’s most critical to our customers. And I’ve spent years talking to our customers so I know them really, really well. I still often find myself speaking on behalf of our customers because of this.
What I’m really saying here is that it all comes down to trust. Take your time hiring a product manager that you trust — someone that you’re comfortable handing your baby over to.
And, once you do hand off product, stay close to the team to keep a pulse on what’s going on so you catch any issues quickly.
2017
The year summarized: We doubled our headcount from about ~25 to ~50 employees. And we moved again — this time into a beautiful offices that we can stay in for years. Signup goals were surpassed more than once. And we went on a second retreat.
The hardest part: We realized our tech was not set up to scale
I’ve established that Roadmunk has grown pretty steadily month-over-month and it’s been an incredible journey… but we weren’t super ready to grow as much as we did in such a short amount of time.
App performance took a hit.
We didn’t realize it was a problem until it was a problem (and hey, this is a problem that many tech companies experience — even Instagram).
Because I was still so entrenched in product management, I was spending so much time talking to customers and trying to make them happy that I neglected to make sure that engineering had a plan in place to scale as needed. And, obviously, performance ended up being a huge customer pain point.
While he have acted on the scaling issue, the hardest part was recognizing that we should have caught it a lot sooner. We should have built better communication bridges between customers, product and engineering.
The most delightful: More good vibes in Nicaragua
The Costa Rica retreat was such a success in 2016 that we took our now much bigger team to Nicaragua for a magical remote-work retreat.
This retreat required an extensive amount of planning given the number of attendees. Logistically, Roadmunk pays for food and accommodation while employees cover flights and local activities. We had workstations, decent wifi and a beautiful view of the beach.
If you’re waffling on whether a trip like this is a good idea for your team, it is — believe me.
We’ve seen ROI from our retreats. The fact that we go on these trips really helps in attracting world-class talent. We’ve produced a world-class team since then because candidates can see that we actually live our core values — instead of just sticking them up on a wall. An A+ team makes investors more confident in our future so they’re more open to fork over more cash (We got a term sheet while we were abroad).
And the month we were in Nicaragua, we had our best sales month up until that point.
The biggest lesson: Hiring people that know more than you will reduce stress levels by a lot
2017 was the year I learned the most. It was full of lessons (mostly because I’ve never managed so many people before) but the one that stands out is the value of hiring experienced team leaders.
Everytime I hired a VP, they had this amazing ability to learn the business at lightning speed, build relationships with key members, surface existing problems and solve them in short order. They were also able to quickly identify areas of growth.
Hiring VPs to lead each department has relieved a lot of stress for me as a CEO. Yeah, I can come up with ideas and start to execute them with different teams, but I don’t have the time to make sure that they’re implemented to scale. VPs can. They’ve been through the ringer to achieve their seniority. Very little phases them. Their lack of stress makes me less stressed.
For example, Andrew Archer, our VP of Growth and Strategy, was brought on in 2017. He started and finished an important project (one that I could not find the time for even though I really wanted to) right away. Within weeks of starting, he led a strategy session to reevaluate and rejig our company vision, strategic objectives and core values.
Thanks to his speedy work to get the whole team aligned, we were all able to start 2018 on the same page.
And I think it’s going to be a great year. 🙂
So, that’s how five years as Roadmunk’s founder/CEO shakes out. And I’m looking forward to seeing what the next five bring. If you have any questions about this crazy business of building startups, shoot me a message on LinkedIn.
