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How I helped Scale an SDR team that led to 600%+ growth and a $21M Series B

June 29, 2020
by
Kyle Vamvouris
Illustration of a boy on a rocket ship.

I was the 24th hire at a small startup company, something that I was unbelievably excited about. I wanted to have a huge impact on the company and I rallied behind their mission. We were going to make a difference.

I was the first manager hire in the sales department, running the sales development team (SDR team). I didn't know it at the time, but this was going to be one of the most impactful experiences in my life.

Rat infested office
Rat infested office

Hockey stick growth, constant change, and incredibly high pressure. I was hired to manage the SDR team that was responsible for generating every meeting conducted by the account executives. My team started with 3 and quickly grew to a team of 12 SDRs fighting daily to hit aggressive metrics.

I loved every second of it.

We started in a small office with rats... literally. In under two years, the company grew by 600%+ and achieved a 21 million dollar series B funding round.

Yes, we did upgrade the office situation along the way.

Every deal closed by the account executives had come from the SDR team. Managing and scaling the SDR team was not easy, but I am proud of how we did it and what the team achieved.

In this article, I'll share some of my story and what I learned along the way.

Learning #1: The core of our success was daily motivation. Not incentives.

There was one situation during my startup experience that really stands out and illustrates the power of motivation. There was less than a week left in the month and my team was behind on their quota by a significant amount, it basically wasn't going to happen. Morale was down and despite my efforts of cheering up the team, they felt down on their luck. Then something special happened.

The entire company was packed in our small conference room for an "all hands" meeting. There wasn't enough space in the room and 10 people had to stand outside and cup their hands over their ears just to hear. I was one of those people.

My boss was giving his update and said: "As for the SDR team, they are not going to get close to hitting quota this month."

My jaw hit the floor, you never claim defeat before the final bell tolls.

I quickly said "hey!" a little too loud as I squeezed passed my colleagues to get into the conference room. The entire company was staring at me and you could hear a pin drop.

I wasn't thinking, I was reacting.

"Don't count us out. Does it look like we will hit quota? No. Not even close. But what I can tell you is that if ANY team can do it, its this one. Do NOT count us out."

The next day I pulled my team aside in the morning and addressed what happened the day before. We all agreed. We were going to make them eat their words.

What happened next was nothing short of amazing. I had never seen my team so fired up. They were cheering each other on, laughing together, and booking more meetings than they even thought possible.

Over the next four days, they broke their "most meetings booked in a day" record twice.

And when the final bell tolled, we were short by one meeting.

You would have thought we had beat our quota by 200%. They didn't care that we missed our team quota by one. They were ecstatic that when everyone in the company thought we couldn't get close, we did.

Incentives are important but they do not replace the ability to motivate a team around an objective.

A team is a group of individuals rallied around a specific objective. Unfortunately, the daily work often has a way of causing the individual to lose sight of that objective. This is very prevalent in SDR teams because the daily work comes with rejection, repetitive tasks, and variables outside of their control.

After that experience, I started spending 10 minutes every morning with my team reminding them of why we are doing this. Pointing at our previous successes and pointing to the potential successes on the horizon. I never stopped motivating the team. I never stopped reminding them of what we accomplished and challenging them to repeat it.

The next month was the biggest one we had ever had.

Incentives are important but they do not replace the ability to motivate a team around an objective.

Action tip: Create a schedule with daily objectives. Share it with the team and motivate them by connecting each daily objective with a larger goal.

Learning #2: Motivation is about narratives, you must create compelling ones.

Motivating my team was necessary because we had to make changes so frequently. There was one change in particular that really stands out. We decided to change our entire target market. yeah, a big decision. Because of this, my team was going to have fewer leads and entirely different messaging. Needless to say, they were going to be less than thrilled. In order for us to be able to execute, I needed to get them excited about the change.

The first step was, I had to be on board. The team leader must believe in the initiative. Fortunately, that was easy. I was totally on board and ready to tackle the challenge.

The second step was, the team needed to understand the reason behind the change and agree that it was necessary.

The third and final step was the most challenging. I needed to motivate the team to execute. This required a strong narrative.

When it came time to tell my team about the change they jumped on board quickly. There were a few concerns that I addressed and then we shifted our focus quickly. I attribute how well received it was to the type of people we hired and to the work I did planning how to deliver the message.

Here is the template I used to construct the message and successfully motivate the team to execute.

The "why" behind this change:

Why us:

What happens when this change is successful:

What this means for them:

How we can exceed expectations:

Startups change a lot. This requires employees to adapt quickly and often. It can be exhausting. Building a narrative around every change is how you can motivate the team and get them on board. This results in them adapting more quickly with less change fatigue.

Action Tip: Expect change, don't just react to it. Create a plan that covers "what to do" and "how to communicate it" for major outcomes (new leadership, hirings/firings, etc).

Learning #3: Take ownership of everything.

When my team was at its peak of 12 people I was managing a lot of different personalities. One rep, in particular, was always late to meetings, skipped out of our one on ones, and intentionally isolated themselves from the team. It was very challenging for me because I liked them a lot as a person but as a member of the team, they were very tough to manage. As their performance slipped I tried to help but it kept getting worse. Finally, they told me that they felt "better than the role" and it all made sense. They were embarrassed to be an SDR because they viewed it as a step back in their career.

Due to poor performance, I ended up having to let go of this employee, something I take very seriously. I reflected on this for a long time as it was my first experience firing someone. It hit me hard.

I wanted to chalk it up to them feeling "better than the role" but I had to take ownership of something to learn and grow from the experience. I reflected on what was in my control and determined that I enabled their belief that they were better than the role. The truth is, at the time I felt that they had more experience than me. My own insecurities were exposed through my actions. I didn't hold them accountable, I didn't effectively communicate my concerns, and frankly...

I didn't do a great job as their leader.

There will always be things outside of your control, it's inevitable. It's easy to point to the uncontrollable variables and assign blame. While scaling an SDR team you must take ownership of everything and focus your energy on what is/was in your control.

I learned from that experience and have never let it happen again.

Action tip: Regardless of the situation take ownership of the result. Find what was in your control, identify what you could of done better, and improve.

Learning #4: Cut poor performers.

While leading the SDR team I got extremely close to each and every one. I felt invested in them as SDRs and as people. I wanted everyone to succeed and I would go to great lengths to help them improve.

But when it came time to cut ties, I would clam up. I tied so much of my success as a manager to the success of each individual on the team, remember the whole "take ownership of everything" thing from above? The idea of accepting defeat by letting go of an SDR crushed me.

Once you've been in a leadership position for a long enough time you learn that the team itself should be looked at as an individual. Once the repetitive actions of one team member hurt the team as a whole a leader must act.

I now follow a simple rule. I put a lot of energy into helping a struggling SDR improve. If they do not take action on my support and continue to perform poorly, I let them go. If they do take action on my support, and still perform poorly, I try to get them a different role at the company. James Collins, in his book Good to Great, says "put the right person in the right seat." If you have a great employee who is struggling in the role, you should find the right role for them.

Action tip: Do not hesitate to cut poor performers. Additionally, if you have the right person make sure that they are in "the right seat."

Learning #5: Hire the right people.

The first group of SDRs I hired was an eclectic group. An international policy expert, Alaskan snowmobile racer, capital investment analyst, and a kid who almost flunked out of college because his kidney exploded. They all shared two things in common. They were very hard working and had a quirky personality that made them stand out.

Hiring is very challenging, especially when you are a startup. A wrong hire costs money but also another valuable resource for startups. Time. There is no debate about the importance of hiring the right people.

My hiring philosophy - Hire hardworking people with unique personalities.

If you are able to stitch together a team of very different people who get along and work hard together you will make magic happen. With so many different types of people, you have access to multiple different perspectives. Mix that with a culture of respectful open debate and the best ideas will rise to the top.

Action tip: When hiring SDRs ask them questions about life outside of work to gage their true personality. Someone's hobbies and interests tell you a lot about them as a person.

Learning #6: Onboarding and training SDRs.

If there is one part of running an SDR team I think is the most important, its onboarding and training. I prioritized having a structured onboarding and training process before everything. The experience an SDR has in the beginning of joining a startup company is directly related to how likely they will stay when things get tough, which they will.

I won't go into the psychology but here is the short reason why. Humans love patterns but in a startup company that changes frequently, patterns are hard to come by. So when there is a tough time and change is occurring, people will cling to any pattern they see. If they received a disorganized onboarding and training program and are now going through a tough time, they may grab on to the pattern of "this company is disorganized and that will make it unsuccessful." If they believe that, why would they stay?

Alternatively, if they had a structured onboarding and training program they are more likely to look at other patterns within their experience and that could be "look at all the good we do for our customers."

What I did was create a structured onboarding, training, and promotion plan. Here is the 30,000-foot view of what it looked like.

Day 1 - Company overview, hardware setup, HR stuff, and competitive landscape.

Day 2 - Prospecting strategy, cold call overview, shadowing SDR calls.

Day 3 - Cold call role-playing, cold calling (yes, I put my SDRs on the phones on day 3).

Day 4 - Day 3 learning, cold call role-playing, cold calling.

Day 5 - Day 4 learning, cold call role-playing, cold calling.

On their second week, they would begin a formal training process that consisted of three tiers.

  • Outbound Prospecting 101 - 3 days a week for 3 months
  • Intermediate Prospecting - 2 days a week for 3 months
  • Advanced Prospecting - 1 day of training, 1 day of teaching prospecting 101 for three months.

Along the way, if they hit specific metrics, they got promoted a total of 3 times. After their third SDR promotion, if they hit specific metrics, they entered a transitional Account Executive role. The reason for this structure is that SDRs want to learn and grow in their career. This structure helped improve their skillset and this growth motivated them to continue to work hard.

Action tip: Create a structured onboarding and training program and STICK TO IT.

Learning #7: Care about their life outside of the workplace.

One of our team goal setting workshops. We did this offsite because… rats.
One of our team goal setting workshops. We did this offsite because… rats.

I believe that the state of your life outside of work impacts your work life. If your outside of work-life is going great, your inside of work-life will follow. If your outside of work life is not going great, your work life will suffer.  This is why I put effort during work to help my teams with their life outside.

One of my favorite activities to do with my team was our personal goal setting workshops. We would all get together in a conference room and spend two hours going through a goal setting worksheet I developed. Here is the high-level outline.

  • Past quarter reflection
  • Past quarter questionnaire
  • Life assessment
  • Future vision writeup
  • Current quarter goals questionnaire

The purpose of this workshop was to help everyone on the team achieve what they are striving for. Just because the goal isn't work-related doesn't mean the company won't benefit from its achievement. If one of my reps wants to lose 30 lbs then I am going to help them create a plan and hold them accountable. I believe that when they are 30 lbs lighter and feeling fit and healthy, their work-life WILL improve.

In addition to having more motivated and fulfilled employees, there is another benefit of helping your SDRs with their life outside of work.

They won't want to leave the company.

Companies that invest in their employees and help them grow as individuals retain those people, that's a fact. By investing in your team and helping them grow professionally and personally they will follow you loyally. Combine that with a team filled with the right people in the right role and you will have an unstoppable SDR team.

Activity Step: Support your team members outside of work. Make sure you spend some time during your 1-on-1s to talk to them about LIFE, not just work.

Learning #8: The SDR role requires routine.

While running an SDR team at a startup company I would meet with the team every morning. The purpose of this meeting was to point out what went well the day before and  where we could improve. Additionally, I would have a specific objective for the current day and rally the team around it. Here is the most important part.

Every SDR must be on board with the objective.

If even one SDR didn't think the objective was reasonable we would discuss. Sometimes the concern was valid and I would adjust the objective. Most of the time I would explain my reasoning, usually backed up by math, and get the SDR on board. This works only if you foster a culture where SDRs feel comfortable disagreeing with management. If they don't, this feedback loop won't occur and your SDR team will be average or below... Not what we are striving for.

After the daily morning team sync, it was off to the races. The SDRs blocked off their schedules to prioritize different activities based on the time of the day. Everyone had a slightly different routine, but here is one example.

SDRs blocked off their schedules for the whole day
SDRs blocked off their schedules for the whole day

Every rep will have a slightly different daily routine, the important thing is that they have one. It’s the manager's job to provide data and guidance to help each SDR develop a routine that is effective for them.

Routines are important in general. Having a morning routine kicks off your day on the right foot and having a planned daily schedule at work keeps everyone more productive.

Being the leader of an SDR team at a startup company requires daily execution. You cannot afford to let bad days turn into bad weeks which turn into bad months. It doesn't fly.

That being said, it is important that the individuals on the team take ownership of their day and dictate their own routine. I find it useful to suggest how each SDR organizes their days but it's their responsibility to build their own routine.

Action tip: Study your top performing SDRs and use their daily routine as an example of what works. Promote this routine to all SDRs so they can use it for guidance when developing their own.

Learning #9: Tracking metrics.

One of the reps on my team was an absolute work-horse. They made more calls than anyone, sent more emails, and always hit their number. This SDR would regularly skip lunch just to get some more calls in. By contrast, I had another SDR on the team who used to make fewer calls, send fewer emails, and they too always hit their quota.

Less activity with the same result? It seemed too good to be true, but it was. I struggled a lot with how to handle the situation. On one hand, I could pressure the SDR with less activity to do more because based on the math they would produce more results. On the other hand, they are hitting their quota so... If it ain’t broke?

As a leader, I believe my job is to set expectations and provide tools and guidance to the individuals on the team to meet them. It’s easy to fall into the trap of what I call spreadsheet management.

Spreadsheet management is when a manager looks at activity metrics and applies results from one rep to the others. For example...

SDR #1 has a 10% conversion rate, makes 80 calls a day, and hits quota every month.

SDR #2 Has a 20% conversion rate, makes 50 calls a day, and hits quota every month.

Spreadsheet management is when the manager tries to make SDR #2 Increase their calls to match SDR #1 because with a 20% conversion rate they would book even more meetings. Spreadsheet management is never the right thing to do because it's not the manager's job to tell their team what to do, it's their job to set expectations and enable the individuals on the team to meet those expectations.

Let me be clear, setting daily activity expectations is important. There should be a minimum activity expectation set for the team, but this should NEVER be more important than getting the result. It's the leader's job to motivate individual SDRs to increase their activities. This can be done with the compensation structure, understanding personal motivators, and/or outside incentives.

Action tip: Focus on results and let the SDRs control how they get there. Only get involved when they are not meeting expectations.

My time building an SDR team at an early stage startup company was the biggest learning experience I have had to date. I have now advised several other start up companies on how to run their teams with great success. The core of my advice comes from the experience of actually doing it. It is not based on theory. It's based on the fundamentals of team building while applying best practices for SDR teams.

It's not easy, but anyone is capable of building a world-class SDR team. Apply some of the learnings I shared above mixed with your own experiences and I truly believe you will have great success.

P.S. If you want help scaling your SDR team through the roof, schedule a chat.

Action Steps

  • Create a schedule with daily objectives. Share it with the team and motivate them by connecting each daily objective with a larger goal.
  • Expect change, don't just react to it. Create a plan that covers "what to do" and "how to communicate it" for major outcomes (new leadership, hirings/firings, etc).
  • Regardless of the situation take ownership of the result. Find what was in your control, identify what you could of done better, and improve.
  • Do not hesitate to cut poor performers. Additionally, if you have the right person make sure that they are in "the right seat."
  • When hiring SDRs ask them questions about life outside of work to gage their true personality. Someone's hobbies and interests tell you a lot about them as a person.
  • Create a structured onboarding and training program and STICK TO IT.
  • Support your team members outside of work. Make sure you spend some time during your 1-on-1s to talk to them about LIFE, not just work.
  • Study your top performing SDRs and use their daily routine as an example of what works. Promote this routine to all SDRs so they can use it for guidance when developing their own.
  • Focus on results and let the SDRs control how they get there. Only get involved when they are not meeting expectations.

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