Lessons Learned Over 4 Months as the Interim Sales VP for my SaaS Startup
I took on the role of Sales VP for my SaaS Startup for 4 months, and here’s how it went. But first, you should know a little bit about me…
For as long as I remember, I’ve been an engineer. My parents were engineers, my sister and nephews were engineers, my grandfather was an engineer. It shouldn’t surprise you that I was a geek as a kid. Big time. I was frequently found disassembling things like VCRs to understand how they’re working. Other times I was building things and giving them to my parents or friends to suggest improvements. I liked putting a lot of thought into designing and building things that would have some kind of impact on people’s lives. If something failed, I’d get emotional and try to beat it into shape until it made sense for me and others.
My first sale
I remember my first ever sales experience like it was yesterday. My uncle Renos owned a store with 20 or so employees which sold linen and curtains and asked me to help him out during the summer. I was 14 at the time and welcomed with open arms the chance to make some extra pocket money. The job included helping with anything under the sun: carrying stuff, hanging curtains in customers’ houses, and (more frequently than anything else) making coffee. What it most definitely didn’t include was sales.
One day, I had to watch the shop for a few minutes without adult supervision. As fate would have it, a customer walks in. She was an elegantly dressed woman in her 50s and I remember her walking with the grace of a member of the royal family. As she was walking in, a feeling of panic hit me like never before. I was suddenly responsible for something of critical importance for my uncle and became engulfed with an overwhelming feeling of accountability. What if she was a hotel manager and needed to place a large order like 800 bed linens? And there I was, a clueless 14-year-old kid fully responsible for helping her.
“May I be of service madam?” I asked, after finding the courage to stand up and slowly walk to her. She looked at me, smiling graciously, clearly recognizing the effort I was making to be professional and courteous, and replied politely, “I’d like to see some silk curtains for my house young gentleman.” We went on and looked at some options, and after 5 or so minutes, I walked her out. As the door closed behind her, along with the pressure of helping her, I was overwhelmed with feelings. My heart was beating fast. It was partly relief, partly a rush of excitement, and partly thinking that I could have done better.
“You did well, son,” said a voice. It was my uncle. He had been watching the whole thing from the deepest corner of the store. He smiled, nodded respectfully, and went back down the staircase to the workshop.
I learned one lesson about sales from my uncle that day. It’s OK not to be certain about what you’re doing the first time. Just give it your best and have fun while at it.
My first role as VP Sales
In September of 2016, we decided our sales team at Transifex needed a new leader. I gave myself 4 months to find the right VP of Sales. Until then, I would jump in and act as our VP of Sales.
Until this point, I’d worked mostly with engineers. What was obvious from the start is that salesmen and saleswomen are wired very differently than engineers. You can find similar characteristics between salespeople and athletes — which is why athletes do great in sales. Engineers are, well, almost the opposite of athletes really. Most of the lessons learned during my tenure as the VP of Sales at Transifex stems from this observation and are shared below.
Lesson #1: The pain is the prelude to the gain
For every tens or hundreds of emails and phone calls, there’s a win. While for other people an unanswered email is a failure, something you would get emotional about, for sales it is a part of the process. It’s a numbers game. It’s like a muscle that needs exercise and many repetitions to get stronger and better before lifting the desired weight.
This is why sales teams thrive with activity. But only having a revenue goal is too high-level to manage properly. It needs to be broken down into daily activities that can be quantifiably measured. If you know general conversion rates, it’s easy to hit your numbers by tracking X ops created and Y activity touches per day.
"Opportunities created per week" is an excellent all-around sales KPI (Key Performance Indicator) to track against: it’s high-level enough to easily correlate to a revenue goal but low-level enough to understand and measure on a daily basis.
I learned that making the effort, even if there are no visible results, is part of the sales process. It makes you stronger, wiser and takes you one step closer to your goals.
Lesson #2: Sometimes you win, sometimes you lose
Some cases are a done-deal. Some need work to help the customer understand the problem and picture how your solution will help them. And some (if not most) are never meant to close.
Here’s what the typical lead probability distribution curve looks like in terms of all deals and how likely they are to close. Each point on the curve represents a specific customer (horizontal axis) and their probability to convert (vertical axis).
We can group the deals into three parts:
- On the right side, you’ve got a few deals which are almost certain to close (their probability is close to 1). These companies have a big need, they know you’re a great fit, they have the budget, and they are excited to go through the process of setting things up. You only need to show up to get them through the door. Just don’t screw up.
- On the left side, you’ve got a ton of leads that have a very low (<30%) probability to close. Your marketing (lead generation) and sales development teams have the responsibility to nurture those leads and help them until the point in time when they’ll be ready to choose a solution like yours.
- And then you have the “Probably want to buy” section of the curve. It’s those customers who are close, but no cigar.
Sales should only work on those few customers that probably want to buy.
Sales is about getting a customer close but yes, with a cigar.
Notice a few things about this part of the curve:
- The width represents a pretty small number of leads compared to the total amount. Yes, pretty small indeed.
- At the same time, its size is at least as wide as the “done deals.” That means that you can double your new revenue if you bring those few accounts (assuming a consistent ASP across the board).
- The curve drops dramatically as you go further to the left. You only have a handful of users in that group, and the variance in the probability to convert is rather large. Some of them are very warm and some others are quite cold. Sales is the process of taking those not-so-certain users, walking them through the process, and making them certain ones.
Working on this segment means that you’ll be working on some deals that might be not inherently ready to buy, already sold on another product, or not have a huge need. There is a big chance of losing accounts that you were hoping to close. Others will close for lower amounts than projected.
I learned that losing a deal is part of the process. It’s part of pushing yourself to achieve more than what’s inside your comfort zone, to close deals outside of your “almost certain” zone. Do not dwell on a lost deal. Be grateful you were considered in the first place because it means you’re on the right track. Learn from the process, rinse, and repeat.
Lesson #3: Always Be Commending
Engineers like to be left alone. If you pay too much attention to them, analyze how they’re working, and instruct in relevant skills, you’ll soon start getting angry looks when you approach their desks. Sales teams on the other hand work closely with their leaders, thrive best when given guidance and encouragement because at the end of the day, the constant beating from lost deals should be overshadowed by the celebration, the praise, and the recognition.
If the salespeople’s ABC is “Always Be Closing”, the good sales leader’s is “Always Be Commending”. Always support your team and be there when someone asks for your help. Stop what you are doing and listen. Your team wants to be successful and close that deal as much as you do, or maybe more. And they know what they need to do. Don’t pull a Glengarry Blake speech on them.
And when a deal doesn’t turn out to be as promising as hoped , don’t ask “why didn’t we sign at the higher price we originally discussed?” Getting scolded will only make that team member feel like you’re not appreciating the effort they put into that deal. Instead, offer support and constructive feedback to make the next deal better. Be a champion for your team and show them the way without condemning or complaining because you will not get the true results you want.
Lesson #4: Salespeople are loud and that’s beautiful
Great sales teams are constantly talking, exchanging ideas with one another and laughing out loud with customers on the phone. Loud noises, for the most part, show that your sales team is “in the zone” and it’s actually what you want from your sales team. In our Transifex US office, we have an open space, so the initial reaction was to ask the sales team to tone it down. Wrong move. Let your sales team do what they know to do best.
Excitement and energy in sales teams are contagious. You want your sales team to experience the whole range of emotions, share the effort, celebrate the wins together. You want the gong.
Lesson #5: Being a VP of Sales requires help
Knowing my background isn’t in sales, I knew that acting as the VP of Sales at Transifex would require help, and I strived and believe any leader should strive to:
- Openly and honestly communicate with all teams. Share with the company you need their help to be successful as a sales leader. Marketing needs to know what you need and they need to know what you need to learn from them. Product needs to know what are the low-hanging fruit (for us it was adding a “Request a Demo” button on the website and redesigning our Pricing page).
- Jump in the trenches yourself. Roll up your sleeves and contribute. And yes, focus on those parts which are least exciting and sexy. Make phone calls, send emails, wake up early to talk to customers across the ocean. Don’t just tell people what to do. Do it yourself first.
- Ask for help. Reach out to people you know who have done the job well. We invited a specialist in demand generation to share their experience with our team and encouraged our salespeople to openly ask for help when they needed it.
My first sales job has come to an end
I acted as the sales VP for Transifex for 4 months and I want to emphasize that “acted” is an apt term for this process. I’ve led many large deals for Transifex since we started, including 6-figure ones, but when I first took on this role, the idea of leading our sales team scared the bejesus out of me. My instinctive feeling was “I’m not made for this. I’m an engineer. It feels so wrong.” Sure, I get excited talking about our product. I can do that for hours. But actually, sell? Darn, that felt hard.
Now that my tenure as the VP of Sales has come to an end, I can confidently say that sales is not for the faint-hearted. If I had to rate myself, I’d be generous and give myself a 5/10. I had to learn fast a lot of things: leading and coaching a sales team on a day-by-day basis, running sales ops, forecasting a quarter, setting up comp plans. And I had a lot of conflicting feelings throughout the process.
The engineer inside me was excited to learn something new and understand how another part of the business worked ground-up. The adventurer inside me was thrilled with the opportunity to work outside of my comfort zone and stretch myself. At the same time, I had moments where I felt again insufficient for what the role required. And it’s then I reminded of what I learned from my uncle Renos:
“it’s OK not to be certain about what you’re doing the first time. Just give it your best and have fun while at it.”