👋🏻 hey there! I’m Alex. I’ve 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 (acq’d by DataDog), Rewind.ai, others, and an LP in Preface Ventures. Oh, I’m currently looking for a new gig and sharing my journey & strategies to find what’s next.
The Ultimate Sales Interview Playbook - Part 2
This is part of my Ultimate Sales Interview Playbook series that I’m 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 it’s absurd, some of those postings have 100-200+ applicants! How the hell can you stand out?
In upcoming posts, I’ll be writing about:
A framework to evaluate startups
Questions from 50+ interviews
Challenges & homework assignments (templates provided)
Strategies to standout & drive urgency
13 Strategies… 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 I’ve partnered with them… both myself and to send them candidates when I have friends looking.
Strategy 1: The VC Referral
If you’ve 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]’s 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
I’ve posted resumes for friends in the “available talent” 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 it’s 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. I’m part of their Sales Core and community if you’d like help.
Strategy 3: Who’s performing best?
You can then ask for an intro and go directly to the company and reference who pointed you in that direction. It’ll also help you optimize for a faster-growing startup and a company that has a better PMF.
The Outbound
If you’re in sales… this is a great way to demonstrate your PG skills. You know what I’m talking about… 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 you’d be a good fit. Good leaders are constantly building their network ahead of open positions. This is actually how I landed a job at Snyk… there was no position listed, but the VP of Sales was interested in a conversation and he knew there’d 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.
You’ll likely have to build one at some point if you’re 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 you’d 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. There’s often a cash bonus in it for them. I typically frame these as “I saw your company is hiring. I’m doing my homework and would love to learn more about what it’s like to work there.”
Recruiter Networks
Strategy 9: Leverage outside recruiters.
Many markets, like cybersecurity, have recruiters that just focus on that domain. I’ve found recruiters have access to job openings that aren’t on LinkedIn or other places. They can also help with job market insights, and how companies are doing, and help point to companies you haven’t discovered yet. You might be missing out if you don’t work with them.
Strategy 10: Ask recruiters where they have connections.
(They don’t have to be under contract, they’ll likely still help you if they’re playing the long game.)
Similarly to sales, recruiters are looking to build relationships and prospect into new accounts. A recruiter that I’ve been working with was open to introducing me to a company that they knew but wasn’t formally under contract. The recruiter may not get any commission, but they’ve 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 don’t have to see a job opening to inquire.
Strategy 12: Write about your experience in public.
I wasn’t expecting this one… but openly posting about this very topic helped start several new conversations and reopened others when I posted I’m doing this series.
There’s something to being vulnerable in public and showing who you are.
I’ll 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.