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. You probably have to hire them one at a time, a bit slowly.

Sales Hiring 299

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 299

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. These are all full-time jobs by $1m ARR.

Part-Time VPE 299

Part-Time VPE Sales Recruiting Sales Hiring Scale 299

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’m doing this thing for the first time. SaaStr is Turning 10!

Sales Hiring 290

Sales Hiring Part-Time VPE VP of Engineering Sales Recruiting 290

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 283

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 283

SaaStr

SEPTEMBER 11, 2021

Lately I’ve been working with 5+ SaaS companies all hiring their first VP of Product. That means often it’s not entirely clear who the first VP of Product should report to. A few general learnings: A VP of Product that Reports to CTO / Engineering Rarely Meets With That Many Customers.

Part-Time VPE 321

Part-Time VPE Outsourcing Services CTO Hire CTO 321

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. – does the team believe?

Part-Time VPE 224

Part-Time VPE Sales Hiring Sales Recruiting Metrics 224

SaaStr

OCTOBER 9, 2020

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. I’ve had to recruit Ph.Ds. Front-end, mid-end, back-end engineers of all sorts and types. Just pass here, nine times out of ten at least.

Sales Hiring 259

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 259

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. She can be your CTO forever.

Scale 279

Scale Part-Time VPE CTO Hire Fractional VPE 279

SaaStr

JUNE 3, 2021

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. You have to love, or at least commit to, recruiting constantly. You have to hire so many functions in SaaS?—?VPS, VPS, VPM, VPP, VPCS, VPE, etc. You will have a Year From Hell here.

Part-Time VPE 299

Part-Time VPE VPCs (Virtual Private Cloud) B2C SaaS 299

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. Q: What’s the number one challenge for scale-up founders?

Part-Time VPE 287

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 287

SaaStr

AUGUST 9, 2023

Ok now that some time has gone by I can reflect a bit more thoughtfully here. My top mistakes as a SaaS founder/CEO: Not convincing the very, very, very best VPE I knew to join as our VPE. I had a great CTO, but I also needed a truly great VPE to scale past $10m ARR and deal with all those issues. Selling the company.

Part-Time VPE 245

Part-Time VPE Sales Recruiting CTO Scale 245

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 321

Part-Time VPE Sales Hiring Sales Recruiting Finance 321

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. And importantly, you need to spend more time with your existing customers (vs. But even if you’ve hired the world’s best VP of Sales … you can’t opt out of sales entirely.

Part-Time VPE 290

Part-Time VPE Sales Hiring Sales Recruiting Outsourcing Services 290

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. The three times it happened to me: A very senior engineer that we just HAD to have. Something organic.

Part-Time VPE 290

Part-Time VPE Sales Hiring CTO Hire Scale 290

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 262

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 262

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. The director that wants a shot at VP.

Part-Time VPE 257

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 257

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 328

Part-Time VPE Sales Hiring Scale Sales Recruiting 328

TechEmpower SaaS

AUGUST 7, 2023

Should a startup CTO spend their time programming? Here’s a graphic from Socal CTO that illustrates the roles as they change over time: In its earliest days, a startup’s top need is often to produce a product. Hiring a hands-on lead developer might seem like the right move for an early stage startup. What does the role demand?

CTO Hire 390

CTO Hire New CTO CTO Fractional VPE 390

SaaStr

SEPTEMBER 10, 2021

And he made an observation to me that I’d been thinking about for a very long time, but didn’t know how to express. And for the most part, these were incredibly stressful times, when I was very underpaid, overworked, and worked to the bone. Not just being part of something great — but, Being Great.

Part-Time VPE 299

Part-Time VPE CTO Hire AWS New CTO 299

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. But I started to learn what it took to recruit, inspire, and yes fail a team. I’m still learning.

Part-Time VPE 185

Part-Time VPE Fractional VPE CTO Hire Sales Recruiting 185

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. You spend all your recruiting time just on VPs and above.

Part-Time VPE 265

Part-Time VPE Sales Recruiting Sales Hiring Startup 265

SaaStr

MAY 16, 2021

But what they don’t have is a good enough founding team: Sometimes, if the prospective founder isn’t super technical, then the CTO/VPE isn’t really great. But great teams find great markets, so that doesn’t really matter}. At least an acqui-hire. As individuals, they are amazing. At least a single.

Part-Time VPE 262

Part-Time VPE CTO Hire New CTO CTO 262

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. They know sales processes, objections, and timings, so they bring in a few deals in the pipe to close faster. Hiring someone too junior.

Part-Time VPE 239

Part-Time VPE Scale Sales Hiring CTO Hire 239

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. If your VPE, or head of marketing, or someone key quits — you’re almost dead. But if you hire one VP after another, it will just take way too long. So first, buck up.

Scale 260

Scale Part-Time VPE Sales Hiring Scaling 260

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. If you aren’t meeting that many, you aren’t taking hiring seriously.

Sales Hiring 311

Sales Hiring Part-Time VPE Venture Capital Fractional VPE 311

SaaStr

SEPTEMBER 7, 2020

Goodness this is one of the toughest parts of scaling. I remember Aaron Levie, CEO of Box, and I discussed this at one of the SaaStr Annuals, when he lost his VP of Engineering. All I can tell you is this: First, if you hire great VPs, it partially takes care of itself. We’ve all lived it. I still live it myself!

Part-Time VPE 207

Part-Time VPE Scaling Engineering Startup 207

SaaStr

MAY 19, 2022

Dear SaaStr: Do My VP of Eng and My VP of Product Have to Be Technically Excellent? A Great VP of Engineering must either: Either have been a truly great IC engineer; and/or. A pretty good IC who still is a hacker and enjoys coding in their free time. This has been pretty much my experience.

Part-Time VPE 288

Part-Time VPE Engineering Management 288

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. Contactually is on the hunt for a VP of Engineering Referral bonus: $1,000 to the referrer and $1,000 to a charity of his/her choosing Tweet it!

Sales Hiring 133

Sales Hiring Part-Time VPE Sales Recruiting Engineering 133

SaaStr

NOVEMBER 10, 2023

Dear SaaStr: What Were Your Toughest Times Before Breaking Out? My toughest times: COO pulling out after signed term sheet — VCs then pulled term sheet. This of course was my fault — I hired the “wrong” COO. Not closing the epic VP of Engineering I really needed. I tried 5 times, maybe 10.

Part-Time VPE 289

Part-Time VPE Banking Engineering Customer Support 289

SaaStr

FEBRUARY 13, 2021

I wrote a piece some time ago here, a person favorite, about Our Year of Hell. When a bad hire at a key time, and some confusion on strategy, led us to our worst year ever on a Year-over-Year growth rate basis. At least some times. I know you may be tempted to spend all your time on sales when sales slows.

Part-Time VPE 289

Part-Time VPE Sales Hiring Scale Business 289

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. Hire the smartest, bestest people you can. Do you take a risk on someone a little more junior than you’d like?

Fractional VPE 279

Fractional VPE Sales Hiring Part-Time VPE Engineering 279

Tom Tunguz

JANUARY 24, 2013

He had hired a recruiter to help him grow his team. But at some point in time, most quickly growing startups will need help forming their teams. One of my partners, Tim Haley, was a top recruiter in the valley for many years and having his experience and expertise has been invaluable. How to Pick a Search Firm.

Part-Time VPE 100

Part-Time VPE Interviewing Startup Communication 100

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 270

Merchant Services Part-Time VPE Sales Hiring Scale 270

SaaStr

JULY 30, 2024

Okta’s VP of Engineering, Monica Bajaj, and Senior Director of Platform Product Marketing, Priya Ramamurthi, share Okta’s playbook to PLG, developer experience, and Enterprise ARR. Adopt At the time of adoption, the user starts to feel confident about the product. Let’s start with product-led growth (PLG). I need this.”

Underperforming Technical Team 287

Underperforming Technical Team Enterprise Scale Payments 287

SaaStr

FEBRUARY 12, 2021

Internships have sparked millions of successful careers, and they can be a valuable talent pool from which companies can eventually hire full-time employees. Interns are a pipeline for full-time talent. Your company could be one of them by hiring ambitious interns. Recruitment Tips.

Part-Time VPE 174

Part-Time VPE Engineering Startup Business 174

SaaStr

MARCH 6, 2024

Founder CEO Todd McKinnon was VP of Engineering at Salesforce and left to start Okta in the depths of the last downturn. Customer Count Up 8% Year-over-Year to 18,950 It’s hard to find net net customers after $1B ARR. You usually have to start here, but as time goes on, you need to bring in partners in most cases. #7.

Fractional VPE 286

Fractional VPE Part-Time VPE Scale SMB 286

SaaStr

JULY 6, 2020

Just go find the VP you need. Go find the VP you really need. I got the VPs of Sales, Product and Marketing I needed. I got the VPs of Sales, Product and Marketing I needed. But I should have taken a pause and just found our true VP of Engineering. You can miss a quarter if need be.

Part-Time VPE 323

Part-Time VPE Scale Finance Market Segmentation 323