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8 lessons from 8 years in SDR Leadership

how to skip the mistakes I made

Chris Ritson

18 Aug 2023

3 min

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Most leaders struggle to handle the pace when they first start out and I was no different. 

I felt like a spare part of the commercial team and more alone than I ever had before in a business. 

I actually ended up nearly quitting a few months into the role. 

Luckily, I swallowed my pride and spoke to my dad. He told me ‘whatever your problem if you stare at the wall long enough you’ll work it out’. 

So stare at the wall I did. 

Fast forward 8 years and I still commit to metaphorically stare at the wall until I work out my problems. 

The point is, if you want something to work, you have to commit to it. Whether that is SDR, AE, or Leadership. It’s just part of life. 

Today, I’ll share 8 lessons I’ve learned that I wouldn’t have if I’d quit, I hope they help you be better leaders. 

Let’s dive in. 

1/ You’re not alone 

As I said when I first started I felt SO alone. I couldn’t confide in my boss and my peers were people I now managed. I felt I had to be ‘strong’ for them. 

Eventually (after I spoke to my dad and wife), I decided to do 4 things: 

  1. Be vulnerable with my direct reports. I showed them I was human not some weird wannabe superhero. 

  2. Find an external mentor. I outbounded people on LinkedIn who were 2/3 years ahead of me. 

  3. I ask other leaders for help. I set up regular 1:1s with top leaders internally and prepared questions for them to help my learning. 

  4. I joined communities online and reached out to people with questions. 

2/ Focus on relentless skill acquisition 

The more senior I got, the more I realized each job change came with a new skill set to learn. 

Committing to the relentless acquisition of new skills is what helped me win new roles before I had even started them. 

I have lived by the rule ‘invest 5% of your earnings back into your development’. 

I’ve read books, I’ve done bootcamps and I’ve paid for 1:1 coaching. 

Setting aside that money for myself was the single biggest reason I’ve had 10+ promotions in my career. 

3/ Delegation is an art 

I’m a mini control freak. I like things done ‘my way’ and I used to not trust people with a whole lot. 

This led to me doing everything and burning out every 3-4 months. It was SO intense. 

Learning to delegate tasks to people who can take them on is a game changer for your own health if not else. 

My top tips are: 

  • Give tasks to people who deserve them (high performers) 

  • Make sure the task is challenging for them but not impossible 

  • Don’t just delegate admin tasks (automate this where possible) 

The benefit will be 2-fold as you won’t have to do it but you’ll also be teaching others how they can. 


4/ Input and Output KPIs are NOT enough 

Ever heard the term ’dashboard manager’? If so, aim to be the opposite. 

Dashboard managers look at inputs and outputs. Number of calls, number of meetings booked etc. 

They often conclude; ‘if we just do more, we will get more' results’. 

This is NOT scalable and not your job. 

Instead, be a leader, look at ‘middle metrics’. Leaders obsess over improving conversion metrics in the sales funnel. 

They know all the details with every single rep they manage and they direct all their coaching efforts towards improving them. 

Why? Because it’s where you can have the biggest impact. Here are a couple of examples: 

  1. Conversion from phone conversation→meeting. 

  2. Email sent→open. Open→Response. 

Here’s another edition you may find useful with KPIs:
5/ Culture is everything 

Building culture is easy. Maintaining culture in a sales environment with lots of pressure is very hard. 

I’ve found culture is built on consistency. 

Consistent behaviours in leadership → consistent behaviours in your reps. 

The higher you go in a business the more people are looking at you for direction. Not just with hard sales skills but also soft skills and how to handle situations. 

For me, this is the single hardest thing to maintain when you’re in the pressure cooker (note; more than a few rewards and shout-outs at the end of the month). 

For example, at Peakon, I wanted a culture of transparency where reps told me their challenges. 

How did we achieve it? I told them my challenges first. 

Whatever I expected from my reps I learned I needed to exhibit and ‘sunshine’ that behaviour first. 

For example; if I wanted reps to feel like taking a holiday was important I’d message the entire group explicitly telling them I booked a holiday because I don’t want to burn out. 

Your job is to show others what they should do, not tell them. 

6/ Coaching should be the number 1 priority every week

On average an SDR Leader spends <5% of their time coaching reps. 

In my early days, I fell into the ‘process trap’ and just tried to build great processes with new tech, almost ignoring the coaching part of my job. 

Then my reps didn’t hit target and I knew it was because they didn’t have the skill. 

I’d failed, not them. 

So I implemented a couple of rules: 

→ 20% of my week will be dedicated to coaching (team and 1:1) 

→ If we identify a big skill gap we train every day until we get it right 

→ No one books coaching over activity blocks in reps calendars 

As soon as I did this, my reps were not only performing better, they were enjoying it more. 

7/ 99% of your success is in who you hire

Hiring is the single highest-risk thing you do as a leader. 

It really doesn’t matter what tech you use, how good your processes are, or how amazing your leadership skills are. 

If you hire wrong, you’re screwed before you start allocating them accounts. 

Trust me, I’ve made a few bad hires in the 250+ I’ve recruited but a lot of them are now top AEs, CSMs, AMs and Sales Leaders across the globe. 

The key is refining what you’re looking for in terms of soft and hard skills and then scoring your interviewees on them. This keeps it fair and data influenced. 

The more predictable your hiring process is the more predictable your results. 

If you want more help with this check out this article:
8/ Your team isn’t your SDRs

Sounds ridiculous doesn’t but your team is not primarily your SDRs. 

It’s the rest of the commercial leadership team. 

I used to be so prospective of my SDRs I accidentally siloed us as a team from the rest of the business. 

That meant it was harder to get what we needed and I ended up not serving them as best I could. 

Your SDR team is your 2nd team. The commercial leadership team is your 1st. 

Align with them, build relationships then you’ll get what you want. 

Only when you do that will you be able to serve your reps best. 

BONUS: Learn the individual, then communicate what you want

10 years ago, my 1st boss used to just tell us what to do and then we had to get on with it. 

He never spent any time getting to know me, how I liked to learn, my career goals, my personal objectives. 

After that, I dedicated my own leadership journey to learning EVERY individual as best I could across my teams. 

I found once I understood them, their goals, their ambitions, and their personal stories I could lead them properly. 

I knew when to push people, who to push more, who to leave alone to crack on with it, and who to put an arm around and support. 

For me, this was part of the relentless focus I had on skill acquisition as I was also focused on learning the soft skills of leadership. 

It’s probably also why I remain good friends with many of the SDRs I’ve hired. 

The aim shouldn’t be short-term results but long-term relationships. 

But remember, it’s a skill that needs to be worked on, day in, day out. 

Quick Summary: 

8 years is a long time in SDR Leadership. It’s had some really tough days. I’ve missed quarterly numbers and lost reps to competitors who I loved! 

But with a deep commitment to yourself, and your development, and accepting it’s about the journey, not the destination you can learn to love this role. 

Now I know what I know, I wouldn’t have it any other way. 

This week’s action step: 

Note down the skills you need to be successful in SDR Leadership then score yourself against those skills. 

Start noting down how you can invest in getting better at those skills or have your business invest in you and your development. 

If you don’t ask your biz for it, you don’t get it. 

Good luck!!

Leader Spotlight:

This week’s spotlight is different. Please meet Georgie Palmer.

Her journey:

Georgie started out in IT Sales (HARD!) smashing the phones and building core sales skills. From there she built out 2x SDR teams and most recently led a team of full-cycle AEs at Florence. 

Like so many super-talented folks this year, she was made redundant recently and is looking for her next gig. 

If you’re looking for an SDR or AE team manager I would recommend you have a chat with Georgie. 

Some of her (many) achievements: 

→ Hired and ramped a team of AEs in 4 months (hit >200%+) 

→ Hired, ramped, and scaled SDR teams → she knows how to generate pipeline 

→ Shes been a top seller herself in previous roles, always exceeding 100% of the quarterly quota 

The cherry on top is she has great leadership soft skills, values collaboration and building company culture, and is a great person to be around. 

Let’s use this incredible community for good! 

If anyone can help Georgie in her search 

Over to you, folks. 

PS. Please see her 

LinkedIn here  

PSS. If you’re looking for a role and want me to include you here for extra exposure let me know. 

Weekly Send-Off:

Naturally, I hope you all have an incredible weekend. I’m driving 7 hours to Switzerland with a 1-year old (wish me luck). 

Until next Friday at 1.05pm, au revoir from me, Bridge and Isaac 🙂 

PS. My number is +447814904622. If you need me, Whatsapp me.

Whenever you’re ready, here are 2 ways I can help you: 

Our September cohort closes today, grab your seat now. 

The last one SOLD OUT in 2 weeks. Our October cohort goes on sale in September. You can join our waitlist on the landing page. + tips

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© 2024 Chris Ritson. All right reserved.

© 2024 Chris Ritson. All right reserved.