Dear SaaStr: I’m Joining a Start-Up as Head of Sales At Just $1m ARR. What Should I Do First?
First off, congrats on the role—it’s a big deal. But seed stage is tough. You’re building from scratch, and there’s no playbook handed to you. And you really are going to have to be both an AE yourself as well as the “boss” for a while.
So let’s get you on track to crush it:
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Master the Product and ICP (Ideal Customer Profile) on Day 0. Before You Start.
You need to know the product inside and out. Not just the features, but the value. What problems does it solve? Why do customers care? Spend time with the product team, sit in on customer calls, and learn the top 10 objections and how to handle them. If you can’t demo the product like a pro within a week or so, you’re already behind. But really, before you start.. Don’t start in fact before you can demo the product for real. You’ll thank me and everyone for it. You almost never catch up, otherwise.Also, get crystal clear on your ICP. Who are your best-fit customers? What industries, company sizes, and roles should you target? If you’re chasing the wrong leads, you’re wasting time.
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Build Pipeline Relentlessly
At seed stage, pipeline is everything. You probably don’t have enough inbound leads yet, so you’ll need to focus heavily on outbound. Roll up your sleeves and prospect yourself. Don’t wait to hire an SDR team—start building pipeline immediately. Use tools like LinkedIn Sales Navigator, Apollo, or ZoomInfo to find leads. And make sure you’re tracking metrics: how many leads convert to meetings, how many meetings to opportunities, and so on. -
Sell Half of The Next $1M Yourself (Or Close To It)
At this stage, you’re not just managing—you’re selling just as much as the likely 1-4 sales reps you’ll inherit and/or hire. You need to close deals yourself to figure out what works. What’s the sales cycle? What objections come up? What messaging resonates? Once you’ve closed a few deals, you can start to build a repeatable process and teach it to others. -
Hire Slowly, But Hire Right
Don’t rush to hire a big team. Start with 1-2 AEs or SDRs who are scrappy and can handle the chaos of a seed-stage startup. Look for people who are hungry, adaptable, and willing to experiment. And don’t outsource hiring—this is your most critical responsibility. If you can’t recruit great talent, you won’t succeed as a VP of Sales. -
Set Realistic Goals and Push Back if Needed
One of the biggest mistakes new VPs of Sales make is signing up for impossible targets. If the CEO wants you to go from $100K ARR to $1M ARR in six months, but you don’t have the pipeline or resources to support it, you need to push back. Agree on a plan that’s ambitious but achievable. Otherwise, you’ll burn out and lose credibility -
Align with Marketing and Product
You can’t do this alone. Work closely with marketing to ensure you’re getting quality leads and that messaging aligns with what resonates in sales conversations. Meet with the product team weekly to share customer feedback and prioritize feature requests. At seed stage, sales, marketing, and product need to be in lockstep. -
Track Metrics and Iterate
Seed stage is all about experimentation. Track everything: conversion rates, deal sizes, sales cycle length, etc. Use this data to refine your process. What’s working? What’s not? Double down on what’s working and cut what’s not. Be ruthless about iterating . -
Be Relentless and Resilient
This is a grind. You’ll face rejection daily, deals will fall through, and you’ll feel like you’re not making progress. But the best VPs of Sales push through. Stay focused on the long-term goal, celebrate small wins, and keep building. - Ask The Tough Questions Before You Start — And Embrace the Tough Answers
Learn where the competition beats you, how much cash runway there is, how many reps you’ll be able to hire, what you budget will be, what the top feature gaps are, etc. Ask everything before you start. It’s OK. Ask.
