In this post, I’ll talk about my 10 month journey of breaking into software sales by landing a Founding Account Executive role at a Seed Stage startup in London.
This period was fraught with a lot of stress, anxiety and learnings but the main focus of this post will be to cover the key takeaways:
Where I Started: Jan 2023
I applied to 50 startup sales roles just to test the waters. Non-serious, mass applications. Nothing highly customised. Just got one initial interview which didn’t go past the recruiter screening call.
I got busy with exam season and also landed a couple internships, so didn’t do much for the next few months apart from that.
Getting Serious: April-May 2023
With business school winding down, I was getting serious about my job search and decided to properly give startup sales roles a shot. It’s why I had moved to London in the first place anyway in Sep 2022.
I googled “types of startup sales jobs” and found a blog which said software sales is the highest growth path. Decided I wanted to do that but needed more information.
To learn more, I went on LinkedIn and Twitter, typed in “SAAS sales”, “software sales” and followed a bunch of legitimate looking accounts.
Next 3 weeks, I started consuming their content. Thing was, they also interacted with other top voices in the Industry and I slowly started surfacing all relevant accounts to follow.
That’s how I was introduced to ‘Gap Selling’ by Keenan. Read the book, made extensive notes and that alone ensured I crushed it in every ‘skills’ interview round I did in the upcoming months.
Of course I did have actual sales chops to back it up from my previous role- but this helped me learn the ‘local lingo’ so to speak as well as learn how the best sellers make strategic moves across a deal cycle and plan for success- many things I wasn’t doing previously.
Side Note: If you want to learn something completely new, I cannot recommend this method highly enough to you Just follow 10 accounts that talk about that topic, and start consuming their content. Make friends with them. Buy their courses I’ve done this with varied topics like AI, D2C businesses (helping a friend launch one), self-publishing, mental health and startup sales.
First Few Interviews: June – July 2023
Interviewed for a few Sales Development Representative roles. This is an entry level role in tech sales. Usually given to recent graduates with 0-2 years of experience. It was something I was overqualified for but the recruiter I worked with convinced me that I’ll only get these kind of roles as my background was in MedTech sales, selling to the government in India.
I noticed that most job applications mentioned SAAS sales experience wanted/desired and understood I was going to have my task cut out in order to break into the Industry, so I went with what he said.
Did a couple interviews- few cut me out of the process because I was overqualified. Others cut me because of lack of SAAS experience. After 1.5 months of interviewing I was back to square one.
By this time, the recruiter stopped responding to my messages so I took matters into my own hands.
I decided to focus most of my time on applying for Account Executive roles- what I felt I was aptly qualified for, with a few SDR applications at companies I really liked.
Second Batch of Serious Applications and Interviews: August – Sep 2023
By this time, I had a good handle on what types of companies to apply for, what do they look for in an application, as well as the first few interview stages.
I had reached out cold to ~50 sales heads in London startups asking for 15 mins on a call. Had a chat with 4-5 and 2 became very close mentors. They essentially helped me craft my CV, and coached me through the first few interview processes I did for Account Executive roles.
I also understood the common objections I got in these interviews- which revolved around me having sold in a completely different sales environment (not SAAS) and in a different market (India).
That’s when I realised that most companies are looking for people with a past record of success in a narrow field. They don’t want someone with a diverse skillset and background. As someone who’s worked very entrepreneurially in his career- this was a major learning, whereas it’s really obvious to most.
Some early stage startup folks I interviewed for GOT IT in but many others just didn’t.
Anyhow- result was I got an interview at a prominent Series A startup in London and at a large tech company.
I spent much of August and September preparing for their multiple interview rounds like crazy.
With the startup, I was eventually cut out in the ‘values’ fit round with the co-founder because they felt I wasn’t motivated enough about their mission and also found someone who had more directly applicable sales experience selling to startups (my background is in selling to large enterprises).
While there was nothing I could do about the latter, the first piece of feedback was I think, the crucial bit I was missing. I needed someone to tell me that, despite my best intentions, sometimes I was unable to translate my curiosity and passion to the interviewees.
Of course a lot of this is subjective, but I looked at every piece of feedback from a lens of : what’s my part in this and what can I action?
With the big tech company, I was the only external applicant from a total of 17 internal and external applicants for the role, that reached the final interview with the VP. Then they finally went with an internal candidate because they already had selling experience with the product.
I was offered a chance to interview for a slightly junior role at the same company, but that was the one skills interview that did not go well. I saw the panel zone out within 10 minutes. Not going deep into that as it’s fairly specific to that job and role but long story short- I didn’t get it.
Back To The Wall: October 2023
I’d invested ~2 months for two interview processes. Learnt a lot but no offer.
Back to square 1.
Applied to a bunch of jobs 1st week of October. Got two serious interviews.
One of them- the HR person rejected me, but I DMd the Sales Head on LinkedIn, he put me through to the interview and liked my profile so much, offered to interview me for a senior role that they hadn’t advertised yet!
Anyway, this month was all about keeping anxiety in check, focusing on the controllables and running the interviews like a sales process. I treated these startups as companies I was selling to.
I did the following:
- Built a point of view on these companies’ offerings.
- Researched their Industry, competitors and regulations – which surfaced a ton of questions to ask them.
- Executed on the skills I’d built from previous interviews as well as improved basis legitimate feedback in places I had screwed up
Offer Received: November 2023
With the first company, I applied on Otta.com (highly recommend- did most of my applications there), and simply went through all rounds of the interview process and got the offer. It was the smoothest interview process I’ve been through so far.
The other startup- the Sales head really liked me after the skills round but the CEO objected to my lack of SAAS experience and I ended up bowing out of the process post that.
The funny thing is- the job I ended up getting was not the interview process I worked hardest for but I knew every step of the way, how to proactively position myself for the best possible outcome.
For instance, while the final interview with the founder was online, I requested if we could do it in-person. I also spoke to the talent acquisition lead on a 15 min call a day prior to understand the CEO’s personality, way of working and areas he might want to talk to me about.
This gave me a lot of useful intel before the meeting and I had genuinely built up a lot of questions to ask the founder about the company that he appreciated too.
I honestly believe that this process went smoothly for me because I had failed and learnt from the 10+ other interview processes as well as prospected other companies, hiring managers like crazy in order to get my foot in the door there. My interview skills were razor sharp and honed, I already had an interview playbook in mind and so, the process went easier than others.
My Process For Applying To SAAS Sales Roles:
- Build a list of companies to apply for- I mainly used Otta.com
- Prioritise them
- Apply to the high priority (P1) roles in one batch. I could usually do 2-3 customised applications in 1 hour along with a DM/email to hiring manager and other people in the same/similar role at the company.
- Apply to lower priority ones after P1s are done – these are less customised or just a basic application + cover letter.
I mainly used Otta.com and a google sheet to keep track of my applications, hiring managers, other ‘peers’ at the companies to seek referrals from, etc.
Key Takeaways:
#1 Reality is bendable.
From starting off interviewing for entry level SDR roles, to getting a role as the first sales hire at a seed stage startup (my sweet spot), I realised just one thing:
As long as it’s not a law of physics, you can bend reality to your will. I (mostly) refused to listen to people who told me to pitch myself in roles I was overqualified for and I’m really proud of myself for that.
#2 Be fanatical about the interview process.
Go into the minute details. From the company, Industry, competitor overview to the interviewees, others on the team, potential challenges for them individually as well as a company… the list goes on.
I treated each interaction like a sales process and had a point of view to share before I even entered the room.
#3 Filter out un-actionable feedback
Separate the chaff and only look at feedback that you can take action on.
This is a painful exercise but learning to use the pain as an indicator of progress rather than a roadblock is everything here. That’s the essence of growth mindset.
And accept the un-actionable feedback. In my case, yeah, it sucked that many hiring managers wouldn’t even look at my CV because of my lack of software sales experience. I couldn’t do anything about that.
So I stopped complaining and went ahead with the journey anyway- because I believed in my skill-set. At my core, I truly believe what my first boss told me- “A seller is a seller. You sell an airbus or a piece of fruit. The fundamentals remain the same”.
Anyway, that’s about all I wanted to share. I sincerely hope that this helps someone out there.
Want To Consult With Me?
If you’d like me to help you step by step to break into tech sales roles, I offering 50 min call slots that you can book here.