SaaStr

DECEMBER 1, 2020

Yes, VCs themselves have to raise the money they invest. Manage existing investments. In addition, in some cases VCs spend a material amount of time interviewing executives and others for portfolio companies. Hint: Most of It Isn’t New Investments appeared first on SaaStr. Let’s break it down a bit.

Investment 222

Investment Interviewing Startup Management 222

Intercom, Inc.

JULY 2, 2020

For Pam, it all stems from a long-held belief that investing in the customer’s success will chart a direct path to the company’s. In the return of the Scale podcast, Pam details her support philosophy and the investments she’s making to drive better customer outcomes, for the long term.

Outsourcing Services 254

Outsourcing Services Investment Underperforming Technical Team Outsourced Development 254

SaaStr

MAY 29, 2025

The CRO Hiring Playbook Has Forever Changed The interview process for revenue leadership roles now at Owner includes a mandatory AI component. Do you invest in upskilling your middle performers, or do you focus resources on amplifying your stars? This creates a talent strategy challenge.

Sales Hiring 231

Sales Hiring Underperforming Technical Team AI Scale 231

SaaStr

MARCH 16, 2025

Force Yourself to Interview 30 Candidates for VP Roles Yes, 30. Use Screening Filters Create simple tests to weed out unqualified candidates before the first interview. Dont wait too long to make this hireits worth the investment. It sounds like overkill, but magic happens when you commit to this.

Software Review 156

Software Review Interviewing Engineering Startup 156

SaaStr

MAY 18, 2025

” Adobe Sign / EchoSign once “failed the due diligence” on a potential sale because their CTO was perceived as not strong enough (despite later becoming a chief scientist at Adobe) “You’re being interviewed and the bet is on the people” 6.

Technical Review 169

Technical Review CTO Hire CTO Sales Hiring 169

SaaStr

NOVEMBER 18, 2021

With nearly a full hour of Q&A with a phenomenal communicator as our guest, our “Off The Record” interview with Pat Grady (Partner at Sequoia Capital) surfaced a number of actionable insights for Founders. We’ve excerpted 10 key highlights from our interview below: #1 – Habits Of Exceptional CEOs.

Scale 335

Scale Company Culture Interviewing Finance 335

Tom Tunguz

FEBRUARY 22, 2025

Interviewers also face a new challenge: developing golden standards to evaluate AI fluency. Of course, this modern interview won’t exclude the other critical components of a high quality process , identifying characteristics of teamwork and sales skills or marketing expertise. 1 Fueled by AI.

Interviewing 113

Interviewing AI Sales Recruiting Construction 113

SaaStr

MAY 6, 2021

Just note, you’ll need a strong balance sheet and stable investments — it takes money to make money. Market: products that aligned with her experience but that she was emotionally invested in and excited about. She used her interviews with investors to find out how they really felt about the product and their why.

Sales Hiring 299

Sales Hiring Sales Recruiting Interviewing Revenue 299

SaaStr

NOVEMBER 15, 2022

But I hadn’t really thought of them as a proxy for all SaaS companies until I saw the CEO’s interview from a few weeks back. Vista’s investments are older, established SaaS companies with brands. The companies they own a majority of are collectively at $24B (!) in ARR, so it’s second only to Salesforce in SaaS.

Cybersecurity 354

Cybersecurity SMB Interviewing Enterprise 354

SaaStr

NOVEMBER 10, 2021

Candid VC Interviews – Session #1 . For our very first session of “Off The Record” we are honored to interview Pat Grady from Sequoia Capital. Pat’s track record includes investments in Amplitude, Drift, Hubspot, Okta, Qualtrics, ServiceNow, Snowflake, and Zoom. Partner | Sequoia. Follow Follow.

Venture Capital 273

Venture Capital Interviewing Investment SaaS 273

FastSpring

OCTOBER 11, 2024

Invest in Customer Support to Drive Retention Retaining annual subscribers requires ongoing support. Meet FastSpring Senior Account Executive Jay Jia and benefit from his expertise about growing a digital goods business in Asia in this deep diving podcast interview. ✦

Merchant Services 158

Merchant Services SaaS Payments Benchmarks Subscription 158

SaaStr

OCTOBER 21, 2020

I took advantage of the format to ask every VC I interviewed one question: Do You Open Cold Email? Personally, I do get behind on email, but I love an amazing cold email and have funded maybe ~50% of my investments from them. And you know, it’s not just me. (I I love a great cold e-mail). All of them do.

Interviewing 351

Interviewing Investment SaaS Sales 351

Intercom, Inc.

SEPTEMBER 22, 2022

At some point in their growth, businesses usually start investing in customer research. No face time with customers, no interviews throughout the product roadmap – just a couple of weeks of user testing before launch. She dove into the world of customer interviews, and just like that, she was hooked.

Interviewing 139

Interviewing Underperforming Technical Team Sales Recruiting Software Review 139

SaaStr

OCTOBER 20, 2022

In my own portfolio , more of my investments had a record month in October than a rough month. They aren’t perfect, but given how many CIOs they interview — over 2,200 for this survey — they’re one of my favorite sources for what’s happening in 2023. But is spending? I’m not so sure. Be honest.

Forecasting 300

Forecasting Artificial Intelligence Software Business 300

SaaStr

MAY 24, 2024

Understanding the Importance of Revenue Goals Jason expresses concerns about the high costs associated with producing a podcast and questions the return on investment if not done thoughtfully. Jason Lemkin has interviewed some of the best founders on his podcast, SaaStr Annual.

Sales Hiring 293

Sales Hiring Outsourcing Services Technical Review Scale 293

SaaStr

MAY 7, 2023

It was a really great deep-dive on where venture is right now: Multiples have fallen back to 2015 and 2016 Why VCs can’t justify investing at $100m+ valuations in many cases today How optimism is bleeding out of VC, and realism has seeped in Why the “next round” often isn’t coming anymore, and how everything got inverted in (..)

Interviewing 291

Interviewing Investment SaaS Sales 291

SaaStr

FEBRUARY 25, 2025

In addition, this year Mayfield is sponsoring our VC AI Pitch Stage and will invest from $500k-$5m in the winner! Many companies strategically use the event to meet potential hires, conduct interviews, and build their talent pipeline. Meet and Find Your Next VP / CXO!

Sales Recruiting 183

Sales Recruiting Scale CTO Hire Sales Hiring 183

SaaStr

SEPTEMBER 11, 2020

Klue , which operates an AI-based competitive analysis platform, announced a $15 million Series A investment this week. The round also saw investments from angels like Frederic Kerrest, who is the co-founder of Okta. . The engagement may last a few months and involve extensive interviews and online research (yes, lots of Googling!)

Consulting 274

Consulting Interviewing AI Innovation 274

SaaStr

JULY 11, 2024

As a startup, most people who come to an interview appear happy. You interview 30 people. If it’s a role you’ve never hired, find someone great at it and have them do your final interview. Are Marketing Agencies Worth Investing In? How Do You Sift Out the Bitter and Broken Individuals When Hiring?

Sales Hiring 285

Sales Hiring Scale Marketing Interviewing 285

SaaStr

MAY 11, 2021

Your best bosses, VPs, mentors and others will give you “audibles” — quick bits of micro-advice during pitches, customer meetings, interviews, etc. If you aren’t investing 20% of your time, you’re doing less important things with that time. But embrace it if you want to be a CEO, a founder, and/or be a part of something bigger.

Scale 293

Scale Compensation Interviewing Scaling 293

SaaStr

AUGUST 30, 2023

They spend most of their time on existing investments. Working with CEOs, recruiting for your existing investments, speaking, events, etc. Just doing VP interviews alone takes a lot of time if you do a lot of them. Best case, that leaves 30-35% of your time to look at new investments. 9 boards x 8 meetings a year x 0.5

Travel 274

Travel Interviewing Investment Business 274

SaaStr

NOVEMBER 16, 2023

For an Investment That is Very Good, But Not Great. We settle when we don’t interview at least 30 candidates for every position. But that’s rare. It’s just so, so hard to truly build something huge and important. Good but not great founders don’t get you there. Good but not great traction?

Interviewing 293

Interviewing Investment Marketing 293

SaaStr

JULY 8, 2020

What Nobody Tells You About Seed Investing with SaaStr CEO Jason Lemkin and Cowboy Ventures Founder and Partner Aileen Lee. I think it gives us a perspective that maybe we don’t get in some other places, in addition to many great investments over the years. Aileen Lee | Founder @ Cowboy Ventures. Jason Lemkin | Founder @ SaaStr.

Investment 199

Investment Technical Review Part-Time VPE Development Team Review 199

SaaStr

OCTOBER 10, 2022

So as I’ve written about before, I’ve interviewed a ton of folks for CS roles in the past 12 months. Most for SaaStr itself (a lot of learnings there, but we have $30m+ of sponsors to keep happy), but also for a number of my investments and more. . — Jason Be Kind Lemkin (@jasonlk) October 9, 2022.

Customer Success 332

Customer Success Sales Hiring Scale Interviewing 332

SaaStr

MARCH 3, 2023

Enablement — setting your team up for success and investing in their professional growth. A designated partner means lower rejection rates at the very first interview. How do you set your team up for success and invest in their professional growth? Invest in enablement. Invest in the right tools to help enablement.

Scale 273

Scale Sales Recruiting Sales Hiring Scaling 273

SaaStr

JUNE 4, 2023

I see very mediocre executives that came into startups I’ve invested in and really get nothing accomplished in 6-9 months or more … then trade that experience for another VP role. It’s time to do them again: First, have the best VP in that role you know interview the VP candidate you want to hire. Again and again.

Sales Hiring 303

Sales Hiring SaaS Interviewing Startup 303

Tom Tunguz

OCTOBER 4, 2019

In a recent interview, Sid Sijbrandij, the founder of Gitlab observed something about remote teams that I think is absolutely true. But in the early days, by virtue of being close to each other physically, it’s easier to delay some of these investments. I’ve seen it in many of the remote/distributed companies we work with.

Startup 252

Startup Interviewing Investment Communication 252

SaaStr

OCTOBER 25, 2023

In this interview, David Sacks talks about how 70-80% of investor time is spent looking at AI. When Lemkin started investing ten years ago, his first five early-stage investments were wildly successful. Talkdesk is worth $10B, and he invested when it was just five people. Q: Should Early-Stage Companies Sprinkle in AI?

Scale 284

Scale Sales Hiring Sales Recruiting AI 284

SaaStr

MAY 5, 2021

I like to equate this stage to Warren Buffett’s famous law of uninterrupted compounding interest—there is a significant difference between investing early and often into an IRA versus starting later in life. . They started off by interviewing internal teams to understand the pain they felt as our product grew and changed.

Strategy 293

Strategy Scale Innovation Interviewing 293

SaaStr

MARCH 22, 2022

This requires effort from your entire organization, and Handshake VP, Employer Partnerships Jessica Peluso outlines some changes that you can make to your brand, and your application, interview, and offer process that will help find the talent you are trying to attract and hire. Below is the transcript of Jessica’s session.

Sales Hiring 261

Sales Hiring Sales Recruiting Scale Sales 261

SaaStr

MARCH 5, 2021

When Garrett interviewed Alex, his challenge was to hire 30 reps within the first 30 days. Do many, many interview rounds. 3 – Invest in your onboarding process. Investing in your CRM and database is key. It’s easy to over-invest in sales and underinvest elsewhere. 1 – Have a recruiting strategy.

Sales Recruiting 249

Sales Recruiting Sales Hiring Scale Sales 249

SaaStr

OCTOBER 30, 2021

A mentor of mine suggested that I reframe my search to seek out companies that I would invest in, instead of the other way around. He told me, you can invest time, talent, or treasure. Unfortunately for me, I had little experience, not much talent, and lacked the treasure/money to invest. It seemed like the best investment! .

Scale 284

Scale Sales Hiring Sales Underperforming Technical Team 284

SaaStr

DECEMBER 19, 2022

As an example, Expensify includes a portion of their interview process where candidates solve a math problem on a whiteboard alongside their potential teammates. At a previous startup she worked for, management was constantly interviewing people from big companies to take leadership roles.

Compensation 261

Compensation Leadership Company Culture Headcount 261

SaaStr

NOVEMBER 2, 2023

Hiring a VP of Sales Who Never Really Understands Your Product During The Interview Process Ok I know some even many will disagree, but I’m right here :). They never invest the time after they start, either. I recently interviewed a seasoned VP of Sales that lived in the South Bay in the Bay Area (San Jose).

Sales Hiring 303

Sales Hiring Sales Recruiting Sales Interviewing 303

SaaStr

MARCH 27, 2022

Interview at least 20 potential customers. This one took me a little while to figure out (thanks to Auren Hoffman for helping me see this clearly), but if you’re a founder, the best investment you can make is in yourself. And I put in a very large capital commitment into investing. And one you truly trust. See here.).

Sales Hiring 362

Sales Hiring Scale Venture Capital Startup 362

SaaStr

FEBRUARY 8, 2021

“A customer who tested the product and did a glowing user interview… then called me back to give more feedback” — Jason Weingarten, CEO/founder Yello. Received 6 unsolicited angel investment offers from ordinary people. .” — Marty Ringlein, Brex. ” — Ryan O’Leary, ListenUpBeat.

CTO Hire 347

CTO Hire New CTO CTO Healthcare 347

SaaStr

DECEMBER 14, 2023

Alison brings the perspective of all sides of a startup, from investing to SaaS to Cloud. For Google Workspace, they invested in expanding and building Google Meet and the rest of the workspace during 2020. It was interesting because they got to interview a bunch of customers and sales executives.

Cloud 309

Cloud Scale AWS AI 309