Thinking back to 2012 when I started in Sales, all I wanted was to progress as fast as possible. 

A sexier job title, more money and the status of being promoted was the most important thing to me. At the time, I didn't know it but it was my first big career mistake. I prioritised progression over learning the skills I needed to succeed when I get there. 

In total I've promoted >10 times. Sounds like crazy growth right? 

Well, the downside was I ‘‘skipped stages’’ in my development. To stay alive in my new role I weekends to catch-up. The pressure got so much I deprioritised my health. I stopped working out, stopped doing things I enjoy and instead started on a path to burn out. 

This week, I’m going to share with you two career stories; 

1. Mine 

2. Tyler Gruca (an SDR Director friend based in the US 

Mine is all about sprint sprint sprint, his is about resilience, logic and patience. 

I hope you can use these stories in your own career planning.

​My Story:

2012 - I started my own business at uni {classic} in the Sports Psychology world. The product was great, the problem was marketing and selling it. As a student with no money, I used Facebook to Cold DM prospects. After a year, around £10k in revenue and 15+ customers later, I quit to ‘‘get a real job’’. 

2013 - My ‘‘real job’’ was as a recruiter in London. I did 327 dials on my first day and >50k calls in year 1. I stuck it out for 18 months and decided to quit to go back to my Sports Psychology career. 

2014 - I applied to 100s of Psychology jobs and got rejected. Frustrated by red tape, bureaucracy and London rental prices I decided to go back to Sales and took a job as an SDR. 

2015 - After hitting quota 6 months in a row I got promoted to AE without a pay rise and given a quota of £20k per month. I struggled to ramp for the first 3 months and got told I had ‘‘one week to make my first sale or I would get fired’’. Luckily, on the Friday, around 2pm I closed a £440 deal {small but it kept me alive}. 

2016 - After I closed that deal things clicked and I pushed for promotions every 3 months moving from AE → Senior AE → Sales Manager → Head of Sales. The business scaled fast and aged 25 I was leading 40+ SMB AEs and responsible for £1M in new business per month {terrifying}. 

2017 - After a year of anxiety, working 18 hour days and taking no vacation I was managed out of the business for being too junior. My rush to the top had finally caught up with me. 

2017 - During my time as an AE Leader I was also charged with building an outsourced SDR team. One thing I found was it was much more effective building the team in house for the scale of pipeline we needed. I also BLOODY loved working with SDRs. So I took a role as an SDR Manager leading a team of 1 SDR. 

2019 - After 2 years of hiring, coaching and scaling an SDR team across 6 regions and getting promoted from Manager → Head of SDR → SDR Director I struggled again to manage the rigours of life at the top. I left (again). Did that stop me though? No. I took another SDR Director at a Seqouia backed start-up {finally I was in the big leagues}. 

2021 - After leading the Global team for 2 years I got a little bored and wanted more. I wanted my own ‘‘growth journey’’ scaling a crazy tech company so I quit to join a startup as a late co-founder. 

2022 - That business didn’t work out. We pushed too hard, spent too much money and it died a painful death. My key takwaway from it all; you don't have to rush everything in your career. 

2022 - After reflecting on my career for 3 months I decided to deprioritise everything I'd fought so hard for. In October 2022, I launched my lifestyle business. 

2024 - Who knows what the future hold? What I do know is I’m chasing happiness now, not revenue. Oh and I’m launching a SECOND business next week. Watch this space.

Tyler’s Story: 

2014 - He was a student-athlete in college. Played Division 1 golf. Graduated with no real work experience but knew he wanted to get into Sales {he had a plan unlike me}. Decided on Tech because it was a growing industry {again, thoughtful} and Atlanta had a great start-up tech scene.

2015 - Tyler then spent 5 months searching for a job. Finally, after a lot of patience, he got hired as an Inbound SDR at Salesloft through a family connection. His first taste of how great referrals are. 

2016 - Salesloft, a start-up then, pivoted. His inbound role became deprecated and he transitioned from an inbound rep to outbound. 

2017 - Frustrated by lack of career progression and was uncertain if he wanted to stay in Sales, he quit on my 2 year work anniversary. 

2018 - He spent 5 MORE month patiently looking for the right job and figuring out exactly what he wanted to do. After some soul searching he realised he wanted to stay in tech sales as he loved the start-up vibes. His former boss hired him as an AE at SaaSOptics in 2018. (In order to get the job as an AE, Tyler first spent 3 months building the inbound GTM process as he did at Salesloft. SaaSOptics even put this in his offer letter. Once he showed that he could qualify and run discovery, they officially made him an AE).

2019 - Like me, he STRUGGLED as an AE at first. Also like me he was told he should look for a new job and threatened with getting fired. Unlike me though he was also told to consider a move into BDR leadership. Also unlike me {I chose to continue as an AE}, he chose BDR Leadership and took on the BDR team w/ 3 reps. 

2020 - Tyler hired his first 2 reps. All of them were bad hires. Had to restart after 4 months. After considering his initial mistakes he got it right the second time around and in H2 of that year I helped grow the team to 10 reps, thanks to post-COVID tech boom. 

2021 - SaaSOptics merged with Chargify. The BDR strategy under the new Maxio brand was all outbound. Tyler took over managing a team of 14 reps. 

2023 - He scaled the team to 18. Promoted two of his Sr. BDRs to Manager and was then promoted to Director himself. 

I also asked him what his biggest challenge was: 

Here it is, in his words: 

‘‘My lack of experience at each stage. Especially early in my career when I had literally zero work experience coming out of college. 

I got over this by taking on responsibilities to show that I could do the job before i got the job.  

Examples: 

• As a graduate, I used outbound strategies like prospect research and outreach to help land interviews and eventually get the job. 

• As an AE, I prioritized building my own pipeline which led to me training others and then being asked to build the BDR org. 

• As a Manager, I took on Director responsibilities by creating frameworks and the delegating responsibilities so I could focus on strategy and scale. This eventually led to a Director promotion.

As the saying goes; ‘there are many ways to skin a cat’. Your career trajectory is no different. 

Whether you’re like me and high execute, or more like Tyler and apply logic and patience to your journey know this; 

It’s not about how quickly you get there, its about whether you ever land at the right destination. So many never do. 

That destination should make you feel fulfilled, happy and like you can do your best work. 

That’s all for this week, if you want to connect with Tyler on LinkedIn, you should. 

PS. If you found this helpful please share with one of your teammates here:

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The Cold Call OS (Behind The Scenes #4): 

This section of the newsletter is a ‘‘behind the scenes’’ view of what has gone into building my new course: 

1. Why I built ‘‘The Cold Call OS’’

2. Who is the Cold Call OS for

3. How I am pricing the Cold Call OS  

4. FAQs 

5. What are people saying? 

Part 4: Frequently asked Questions: 

1. Who is this for? 

It’s for individual contributors who need to cold call to build pipeline and book meetings. Whether you’re an SDR or an AE. If you cold call, this was created for you. 

2. Can I get my money back? 

No. This programme is not refundable. I built this specifically for people who want to improve their cold call skills and take action, if you’re on the fence about that, this isn’t for you. 

3. Can I have a discount code? 

Yes, we update discount codes periodically. The best way to find the current code is to click on the course link directly.

Hope this was helpful.