SaaStr

SEPTEMBER 10, 2020

Perhaps the single most important thing you can ever do in SaaS, at least after $1m in ARR or so, is hire the best VPs you can. We’ve talked a lot over the years about how not to hire a wrong VP of Sales — 70%+ of the first VPs of Sales don’t make it even 10 months. Talk to them.

Part-Time VPE

SaaStr

FEBRUARY 1, 2021

That you absolutely, positively, have to only hire “Rockstars” in your startups. A Rockstar engineer really is 10x better than the next tier. And a Rockstar VP is really what you need in every position. So I’d hire earlier here rather than wait. The very best of the best. It’s true.

Sales Hiring

SaaStr

AUGUST 19, 2021

Q: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $1m-$2m ARR. IME, rough order to make hires in: VPM: $0.2m

Sales Hiring

SaaStr

SEPTEMBER 26, 2022

Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $5m ARR, and ideally, Sales and Marketing well before that.

Sales Hiring

SaaStr

MAY 5, 2021

Did you hire a good enough VP? 4 part test: – who great did they hire in the first 60 days? – did they take part of the job off your plate? If they don't pass the 4 part test, they aren't good enough. Hiring your VPs as a founder is tough. Sales — for a VPS.

Part-Time VPE

SaaStr

SEPTEMBER 24, 2020

You know how everyone says you'll never look and wish you'd kept a bad VP as long as you did? That when you make a mis-hire, you'll always look back and say you should have made a change 3-4 month earlier? A lot of classic SaaStr advice has been how to spot the best potential VPs. When to hire them.

Sales Hiring

SaaStr

OCTOBER 9, 2020

A VP of Sales and Success A VP of Sales and Marketing A VP of Sales and Anything Else. Is usually not really a VP of Sales. I don’t know about you, but I’ve had to recruit a lot of types of folks over the years where my domain knowledge was limited. You get the picture.

Sales Hiring

SaaStr

JANUARY 27, 2021

Especially the money part. We recently did a New New in Venture event and I asked the question of many top VCs including David Sacks, Keith Rabois, Aileen Lee and more. “Give the VP of Sales More Time” This is always terrible advice. In one sales cycle, or less. As CEO, you need to find a way.

Part-Time VPE

SaaStr

MARCH 7, 2021

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. Yes, you can manage the sales team yourself.

Part-Time VPE

SaaStr

MARCH 24, 2021

But I think the biggest, #1, mistake successful first-time entrepreneurs in SaaS make time and time again these days is they micromanage too long. I think it’s a byproduct, in part, of the fact that founders are just so much better these days. Engineering. Go hire them. In every single function.

Part-Time VPE

SaaStr

APRIL 7, 2021

The first type is the kind of management team hired by second+ time founders. Often folks they convince to once again be a VP of Eng or VP of Sales. But most of us are first-time founders, or close to it. But most of us are first-time founders, or close to it. Veterans of the SaaS journey.

Part-Time VPE

SaaStr

JUNE 23, 2020

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. You’ll need more than 5–6 core engineers to go big. She can be your CTO forever.

Part-Time VPE

SaaStr

NOVEMBER 29, 2020

An organization that has come together voluntarily to take on a mission, at least in part. They’ll revolt when you make a senior or mid-level hire that as a group, they simply cannot suffer one day longer. It’s happened to me, and I think for whatever my faults, I have a pretty high EQ and am a half-decent manager.

Part-Time VPE

SaaStr

MARCH 1, 2024

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales.

Scale

SaaStr

DECEMBER 28, 2019

Pick a few that work for you: Get That Key VP Hire Done in Q1. Enough with the excuses for not having hired your real VP of Sales, or that VP of Engineering, or whatever. Hire a real recruiter. Drop other stuff to get this hire done. But anyhow — in January, find a way.

Part-Time VPE

SaaStr

AUGUST 13, 2024

1: Don’t hire a VP (or anyone in the early days) that you aren’t 95% sure is great. Founders between a million and $250M are talking about lowering the bar for hiring because they aren’t sure if the person is great or they’re trying to fill a gap. A great Head of Sales will move the needle. You can’t do that.

Sales Hiring

The Angel VC

JANUARY 4, 2015

At the beginning of December we had the idea that it would be cool to put together a "recruiting advent calendar" with job openings from within the Point Nine Family. Contentful has an open position for a Sales Manager Referral bonus: A weekend trip to Berlin! Do you know a VP of Marketing for Gengo ? Tweet it!

Sales Hiring

SaaStr

JANUARY 22, 2021

As you try to hire up for your SaaS company, you’re going to be faced with a lot of choices and trade-offs. No hire is the perfect package. You can spend more time with prospects. Customers will expect more services, more account management, more configuration. One VP of Product. One VP of Marketing.

Fractional VPE

SaaStr

AUGUST 23, 2022

My general learnings: By 20-30 employees, you should have 1-2 good managers in place such that at least 50% of the company can run based only on weekly staff meetings, 1-on-1s, and “grab me when you need me-s” E.g., a great first VP of Sales that can just handle sales. management team by 50 employees or so.

Part-Time VPE

SaaStr

JULY 5, 2019

We then had our own mini rocketship, hitting challenges and being acquired, and then being part of an IPO. But I got to part of the management team and make mistakes, and work cross-functionally with the other leaders and managers. Third, I then managed a small team. And I learned to recruit.

Part-Time VPE

SaaStr

AUGUST 25, 2023

No one has time to have coffee with all of those folks. 2 “Give the VP of Sales more time.” You can’t always expect a great VP of Sales to double sales in 30-60-90 days. But you have to see progress in one sales cycle. The best VPs of Sales hit the ground running.

Part-Time VPE

SaaStr

JUNE 11, 2019

And that’s really good when you’re scaling part of the team that looks like yourself. So if you’re an engineer and you need more engineers, having a network of engineers is an awesome thing. You don’t know where to find them. You guys are awesome. You don’t know how to interview them.

Merchant Services

SaaStr

NOVEMBER 12, 2020

you don't know what to do: 1/ Spend more time w/existing customers. 2/ Hire 1 great VP. 4/ Join more sales calls. Those are good times indeed. But there will be times when almost all of just not only struggle … but are just sort of out of ideas. Spend more time with existing customers.

Part-Time VPE

SaaStr

DECEMBER 18, 2020

Todd McKinnon, CEO of Okta, for the first time joined us at a SaaStr event, SaaStr Scale 2020. Customers believed in the early days — but many investors and potential hires often didn’t. But VCs and many potential hires thought the space was too small and simple in the early days. That is was “just a widget.”

Part-Time VPE

SaaStr

JUNE 23, 2019

And that’s really good when you’re scaling part of the team that looks like yourself. So if you’re an engineer and you need more engineers, having a network of engineers is an awesome thing. You don’t know where to find them. You guys are awesome. You don’t know how to interview them.

Merchant Services

SaaStr

JUNE 25, 2019

But with it comes immense benefits and competitive advantages such as the diversification of ideas, speedier product development, and representation in important regions and time zones. We got a chance to celebrate our initial public offering on the New York stock exchange back in September, which was a really exciting time for me.

Engineering

SaaStr

JUNE 28, 2020

” In this episode of the SaaStr podcast, Aileen and SaaStr Founder Jason Lemkin take a deep dive on how Aileen finds deals, her tips for a winning pitch, and the state of VC in 2020. 347: Ready to hire your first VP Sales? You can see the full video here , and read the podcast transcript below. Aileen Lee: Yeah.

Part-Time VPE

SaaStr

JUNE 1, 2021

As part of the run up to 2021 SaaStr Annual in the SF Bay Area Sep 27-29 , we’re taking a look back at some of our favorite classic sessions. (And You’ll find out tomorrow. Another piece of very, very good startup advice that I’ve given myself a hundred times is the “Do one thing exceptionally well.”

Part-Time VPE

SaaStr

OCTOBER 14, 2019

I know we all agree everyone in sales has to have commissions and a highly variable comp structure. But — I mean everyone that materially impacts the plan should have some variable comp. “Nah, my Director of Engineering doesn’t need variable comp” you say. At a time the world was ending.

Sales Hiring

SaaStr

JULY 8, 2020

We’ll have some time. It sounds minor or technical, but if you want to due diligence on a human being, I get to do it a few 100 times a year. I used it in kind of my breakfast pre warm-up, the crazy times we’re in. From Satya from Homebrew, we just heard that seed’s at an all time high.

Investment

OpenView Labs

OCTOBER 11, 2019

Pricing is an incredibly important part of any SaaS product’s go-to-market strategy. At Hired, we started out with a transactional model that was—at the time—a super disruptive approach and one of our key differentiators. I’ve had roles in almost every function from sales to product to customer success.

Sales Hiring

SaaStr

APRIL 4, 2019

They wanted real-time results. And so we actually had to make some major adjustments and look for an alternative way to deliver the software which clearly meant that we needed to move to the cloud full-time. Traditionally we’ve been around since 2005 and traditionally have been a software on-prem business. How can you automate?

Cloud

Outseta

MAY 8, 2020

I find that refreshing. Beyond just being smart, I’ve routinely come across people in tech that are tenacious, objective, and have high emotional intelligence—so much so that I often find myself thinking, “It’s too bad so many of these smart people are building email marketing software!”

Part-Time VPE

SaaStr

JULY 12, 2022

As part of that, we wanted to look back at some of our most iconic content and sessions. One of the first what How to Hire a Great VP of Sales at the New York Enterprise Tech Meet-Up (thank you to John Lehr and Work-Bench for setting this up). I don’t know anything about sales. SaaStr is Turning 10!

Sales Hiring

SaaStr

DECEMBER 16, 2023

A mediocre tech team, a part-time CTO, or even just a decent CTO just doesn’t get you there. Wait until you find a great partner here. Finally you have great customers and traction — but you can’t afford to hire all the people you need to meet their needs. If you can’t do the time, don’t do the startup.

Part-Time VPE

SaaStr

MAY 3, 2021

And if your team knows how to spend it, correctly — find a way to get them the capital they need to grow even faster than plan. A new edition, new services, an outbound sales team, an account management / upsell team. And importantly, you need to spend more time with your existing customers (vs.

Part-Time VPE

SaaStr

FEBRUARY 2, 2021

But it turns out, the hardest part isn’t the Magic and the Impossible. The hardest part is this phase: the Possible, But Painful. You’ll have a real sales team, the core of one — but not a large enough one to experiment, or add redundancy, or management layers. At least, hire 2 VPs at a time.

Scale