SaaStr

JANUARY 19, 2022

While there is no legal definition for CTO or bright line between CTO and VPE, I’d suggest a start-up CTO really only has to do a few things — which are very hard: Assemble a small team (3–9) of very good engineers. That often were never anticipated and aren’t part of the job spec. Dear SaaStr: What Makes a Bad CTO?

CTO Hire 298

CTO Hire Part-Time VPE CTO Engineering 298

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

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 290

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 290

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

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

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 310

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 310

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 246

Part-Time VPE Sales Recruiting CTO Scale 246

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

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

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 282

Part-Time VPE Sales Hiring Sales Recruiting CTO Hire 282

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 269

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 269

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

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 206

Part-Time VPE Fractional VPE CTO Hire Sales Recruiting 206

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

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 271

Part-Time VPE Sales Recruiting Sales Hiring Startup 271

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 230

Part-Time VPE Engineering Scaling Startup 230

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 242

Part-Time VPE Sales Hiring Scale CTO Hire 242

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

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 289

Part-Time VPE Engineering Management 289

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

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

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

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 191

Part-Time VPE Engineering Startup Business 191

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 274

Merchant Services Part-Time VPE Sales Hiring Scale 274

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 288

Underperforming Technical Team Enterprise Scale Payments 288

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 329

Part-Time VPE Scale Market Segmentation Finance 329

SaaStr

NOVEMBER 12, 2020

you don't know what to do: 1/ Spend more time w/existing customers. 2/ Hire 1 great VP. 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. Hire 1 great VP.

Part-Time VPE 281

Part-Time VPE Sales Hiring Churn Engineering 281

Tom Tunguz

NOVEMBER 3, 2014

Meanwhile the equity stakes of founding VP of Engineering and VP of Product have remained relatively constant throughout the same five year period across all stages of company. Another cohort has a founding CEO and VPE. Another group has a founding CEO, VPE, VPP and so on.

Part-Time VPE 100

Part-Time VPE Startup Venture Capital Entrepreneurship 100

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 220

Merchant Services Part-Time VPE Sales Hiring Scale 220

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 287

Fractional VPE Part-Time VPE Scale SMB 287

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 231

Part-Time VPE Sales Hiring Scale Cloud 231

SaaStr

APRIL 29, 2019

Check out the line-up… “How to scale your engineering team” with Scality VP of Engineering Pierre Derome. How to give feedback to your teammates ” with Back Market Senior Engineering Manager Nicolas Tricot. How to set up a great hiring process” with Happn VP of Engineering Sebastien Preneta.

Part-Time VPE 175

Part-Time VPE Scale Engineering B2B 175

SaaStr

OCTOBER 12, 2020

SaaStr favorite Tomasz Tunguz of Redpoint Ventures was gracious enough to sit down with Nick Caldwell, former CPO of Looker and current VP of Engineering at Twitter. Nick has vast experience when it comes to B2B and B2C, which is why we asked them to share their best tips for growing product and engineering orgs from 0 to IPO.

Engineering 289

Engineering Part-Time VPE Scale B2C 289