šš» hey there! Iām Alex. Iāve spent 15 years in tech sales at early-stage startups (6 Series As & counting). Some have been home runs (Acquia & Snyk), and some not so much. On the side, I dabble in angel investing, advising early-stage companies, and write here about GTM strategies, frameworks, tech trends behind startups, and learnings along the way. Investments: Dooly.ai, Cake.ai, Digraph (acqād by DataDog), Rewind.ai, others, and an LP in Preface Ventures. Oh, Iām currently looking for a new gig and sharing my journey & strategies to find whatās next.
The Ultimate Sales Interview Playbook - Part 2
This is part of my Ultimate Sales Interview Playbook series that Iām assembling from experience. The following strategies have helped me land interviews in the past several months without applying to job postings. Yes, you still gotta play that game - but itās absurd, some of those postings have 100-200+ applicants! How the hell can you stand out?
In upcoming posts, Iāll be writing about:
A framework to evaluate startups
Questions from 50+ interviews
Challenges & homework assignments (templates provided)
Strategies to standout & drive urgency
13 Strategiesā¦ LFG.
The VC Playbook
VCs differentiate by providing value-added services on top of the capital that they provide to their portfolio companies. Recruiting is one of these services and you can create a win/win for you and them.
This is how Iāve partnered with themā¦ both myself and to send them candidates when I have friends looking.
Strategy 1: The VC Referral
If youāve worked at a venture-backed company, reach out to the previous investors. Provide a summary of your success at that company and point out which portfolio companies & roles are of interest. (They all have job boards.) The referral from the VC to the company can easily put you at the top of the resume list.
Hi Brad,
I worked at your portfolio company Snyk for 3 years in sales.
Your portfolio & job opening [insert posting] caught my attention. [Insert VC name]ās investments are always the most interesting for your thesis around developer tooling.
My background in the developer tooling and security spaces would be a good fit at [insert company], especially contributing insights from the GTM motions at Snyk.
Would you be able to connect me to [insert name] over there?
Thanks,
Alex
Best done over Linkedin.
Strategy 2: VC Slack Communities
Iāve posted resumes for friends in the āavailable talentā channel several times, resulting in job offers at their portfolio companies. This one is a bit harder to uncover, but if the firm has a community manager, then itās likely they are doing something along these lines. This works best for VCs that build local networks.
The Underscore.vc team does a fantastic job of making connections within the Boston startup ecosystem. Iām part of their Sales Core and community if youād like help.
Strategy 3: Whoās performing best?
You can then ask for an intro and go directly to the company and reference who pointed you in that direction. Itāll also help you optimize for a faster-growing startup and a company that has a better PMF.
The Outbound
If youāre in salesā¦ this is a great way to demonstrate your PG skills. You know what Iām talking aboutā¦ cold outbounding. It still works.
Strategy 4: Connect with the leader of the department on LinkedIn.
Then send a brief note explaining your background and hypotheses as to why youād be a good fit. Good leaders are constantly building their network ahead of open positions. This is actually how I landed a job at Snykā¦ there was no position listed, but the VP of Sales was interested in a conversation and he knew thereād be positions opening up.
Strategy 5: Do the same thing as 4, but do it at the Founder/CEO level.
The goal here is to get referred to the right person and mention who you sent your way.
Strategy 6: Send your territory plan.
Youāll likely have to build one at some point if youāre in sales. I highly doubt that 99% of applicants proactively send a customized deck to the company. 80% can likely be templatized for easy reuse.
The Bottoms Up
Strategy 8: Informational interviews with the team.
This approach starts by reaching out to team members youād be working with. Informational interviews can provide you with better insights. Then apply to strategy 4 or ask to get that person to refer you. Thereās often a cash bonus in it for them. I typically frame these as āI saw your company is hiring. Iām doing my homework and would love to learn more about what itās like to work there.ā
Recruiter Networks
Strategy 9: Leverage outside recruiters.
Many markets, like cybersecurity, have recruiters that just focus on that domain. Iāve found recruiters have access to job openings that arenāt on LinkedIn or other places. They can also help with job market insights, and how companies are doing, and help point to companies you havenāt discovered yet. You might be missing out if you donāt work with them.
Strategy 10: Ask recruiters where they have connections.
(They donāt have to be under contract, theyāll likely still help you if theyāre playing the long game.)
Similarly to sales, recruiters are looking to build relationships and prospect into new accounts. A recruiter that Iāve been working with was open to introducing me to a company that they knew but wasnāt formally under contract. The recruiter may not get any commission, but theyāve added value and built a stronger relationship. Find the right recruiters who play the long game.
Your Network (duh)
Strategy 11: Reach out to your network & former colleagues.
Have them check with their leaders to see if any openings are coming up soon. You donāt have to see a job opening to inquire.
Strategy 12: Write about your experience in public.
I wasnāt expecting this oneā¦ but openly posting about this very topic helped start several new conversations and reopened others when I posted Iām doing this series.
Thereās something to being vulnerable in public and showing who you are.
Iāll be writing about a framework I use to evaluate startups (that will also help inform questions you can ask to interview the company.)
Happy hunting and good luck out there. Keep your head up.