SaaStr

MAY 10, 2021

There’s one theme we’ve reiterated over the years, at least since 2017 or so when we interviewed the CEOs of Twilio and Veeva back-to-back : To grow quickly after $100m ARR, you probably need a second core product. Pretty good for SMB SaaS. Box at $800m ARR is about 30% SMB / 70% enterprise, the inverse of Shopify.

Merchant Services 261

Merchant Services SaaS Payments SMB Payment Solutions 261

SaaStr

MAY 10, 2024

Keep Your Hiring Standards High Interviewing is believed to be the most predictive part of the hiring process, but it actually isn’t. Part of the reason we fail at this is the average interview is only about 10% better than flipping a coin and predicting job success. Scored – all interviewers use a scorecard.

Sales Hiring 245

Sales Hiring Scale Sales Interviewing 245

SaaStr

JANUARY 21, 2020

It’s an SMB SaaS company in the healthcare technology vertical. When I’m hiring salespeople, I take the mission, vision, values, whether it’s helping practices thrive, whether your values are speak up, work hard, tying those into interview questions. Do they peel the onion back during the interview?

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

SaaStr

OCTOBER 20, 2022

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. And they say 2023 will be a banner year for enterprise software spend at least — growing a stunning 11% to $880 Billion.

Forecasting 303

Forecasting Artificial Intelligence Software Business 303

SaaStr

MAY 4, 2022

For SMB, it could be $20m-$30m in ARR. So a top theme across SaaStr CEO interviews since 2017 or so, and across our 5 Interesting Learnings series with public SaaS companies, is … when should you go multi-product? Freshworks is another interesting SMB example of going multi-product early. jasonlk) April 29, 2022.

Scale 309

Scale SaaS SMB Scaling 309

SaaStr

OCTOBER 30, 2021

Their CEO will join us at SaaSr Scale 2021 on December 15 to talk about using data to get to 10,000 SMB customers! I asked Aasif Osmany to share his learnings as a top-performing SMB VP of Sales, below. I sent cold emails and LinkedIn messages and ended up with nine interviews. From those nine interviews, I received four offers.

Scale 287

Scale Sales Hiring Sales Underperforming Technical Team 287

SaaStr

SEPTEMBER 1, 2023

But the metrics, especially for an SMB-focused SaaS business, are breathtaking. At SaaStr we’ve been super fans for a long time and a little ways back we did an amazing interview with CEO Andrew Bialceki here: Our 5 Interesting Learnings here: #1. Getting above 100% NRR from true SMBs is tough.

Scale 286

Scale SMB Sales Hiring Interviewing 286

SaaStr

SEPTEMBER 7, 2023

At least 90% at a base case onboarding in 30 days, ideally much faster if you sell to SMBs. Klaviyo for example hits 90% activation in 30 days even with 100,000+ SMB customers and $600m in ARR. Try to get every single customer to fully be on-board within 30 days in general — or much faster for many apps.

Sales Hiring 296

Sales Hiring SaaS SMB Churn 296

SaaStr

MARCH 3, 2023

A designated partner means lower rejection rates at the very first interview. For SMB mid-market, it’s typically around 2-3 months. At Figma, the interview process is the same for salespeople and sales leaders. You can watch for negativity based on candidate answers and feedback during recruiting.

Scale 276

Scale Sales Recruiting Sales Hiring Scaling 276

Sales Hacker

APRIL 21, 2020

You’ll be able to download the interview scorecard template that I use with my clients. Part two of this scorecard series will help you create a sales interview scorecard to land that sales role you’ve been dreaming about. Who is involved in the interview process, onboarding process, and ongoing support and training process?

Sales Hiring 125

Sales Hiring Interviewing Sales Recruiting Underperforming Technical Team 125

SaaStr

MARCH 19, 2021

Armed with these first-hand interviews along with a ton of research, we were able to clearly define our different customer segments along with the roles and responsibilities within each of those segments. Unlike our SMB customers, midsize businesses tend to have multiple key decision makers, including finance, product, IT, security and legal.

Scale 287

Scale Business Finance compliance 287

SaaStr

APRIL 4, 2022

Performance Marketing: Performance marketing focuses on driving volume and velocity through owned and paid ‘always on’ programs for net new leads acquisition for self serve, SMB, and enterprise accounts horizontally. . Affecting change in the sales ecosystem.

Scale 276

Scale Revenue Scaling Marketing 276

SaaStr

AUGUST 8, 2019

The first step in success with SMB clients is to recognize that it’s not a one size fits all scenario. Companies need a specialized approach for SMB accounts, different than the tactics used for Enterprise. I’m very happy to talk about SMB sales today because if you think about it, healthcare is a very nice economic sector.

Sales Recruiting 126

Sales Recruiting SMB Scale Sales Hiring 126

SaaStr

SEPTEMBER 24, 2020

How to interview them and qualify them. SMB reps doing enterprise deals. Well, everyone is right. — Jason ?BeKind? jasonlk) September 24, 2020. A lot of classic SaaStr advice has been how to spot the best potential VPs. When to hire them. What they really do. Some classics here: How My VP, Sales Doubled Our Sales in 90 Days.

Sales Hiring 269

Sales Hiring Part-Time VPE Scale Underperforming Technical Team 269

Sales Hacker

APRIL 8, 2025

Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade. The GTM Podcast The GTM Podcast is a weekly podcast hosted by Scott Barker, GTMfund Partner, featuring interviews with the top 1% GTM executives, VCs, and founders.

Scale 69

Scale Sales Hiring Scaling Revenue 69

SaaStr

AUGUST 8, 2019

The first step in success with SMB clients is to recognize that it’s not a one size fits all scenario. Companies need a specialized approach for SMB accounts, different than the tactics used for Enterprise. I’m very happy to talk about SMB sales today because if you think about it, healthcare is a very nice economic sector.

Sales Recruiting 112

Sales Recruiting SMB Scale Sales Hiring 112

SaaStr

JANUARY 3, 2024

Shrav added that if you want to close bigger deals, not just Enterprise, but mid-market and SMB as well, that the moment you’re ready to Go-To-Market, you need to become compliant. “A lot of the messaging on the SMB side is around, ‘Hey, let’s get you SOC-2 compliant.’

AI 159

AI SMB Sales Hiring compliance 159

FastSpring

SEPTEMBER 16, 2022

In two one-hour interviews, FastSpring sales leaders Todd Stellfox and Tony Markov each interviewed Kurt about pricing strategies that work in volatile markets and beyond. Stream both interviews below and see highlights from each. How FastSpring’s platform allows companies to test their pricing (2 minutes): Full Videos.

Pricing 146

Pricing Payment Solutions Payment Services Scale 146

Sales Hacker

OCTOBER 17, 2023

Prior to starting Blueprint in 2020, he worked for over fifteen years in various sales and sales management roles, building teams across presales, partnerships, SMB, Mid-Market, & Enterprise Sales. Chuck lives in the Bay Area with his wife and has two daughters, a junior at UCLA and a freshman at UC Santa Barbara.

Sales Hiring 127

Sales Hiring Sales Recruiting Interviewing SMB 127

Andreessen Horowitz

APRIL 23, 2024

They also talked about the difficulties — and potential advantages — of selling into small businesses, taking alternative approaches to interviewing candidates, and the importance of keeping culture a vital part of a company as it scales. Both of you sell into SMBs, which is a notoriously difficult segment.

Payments 110

Payments Forecasting Payment Services Sales Hiring 110

SaaStr

JANUARY 24, 2024

Scaling Enterprise vs. Mid-Market Sales: Key Takeaways from Calendly It’s a common blueprint to start with SMB and mid-market accounts as your ideal customers. It requires infrastructure to support your sellers in getting through those tasks.

Scale 276

Scale Sales Hiring Scaling Revenue 276

Sales Hacker

APRIL 15, 2019

He also gives us a framework for how to move upmarket, and the requirements for taking a company from the SMB space all the way to the enterprise. Strategies for moving upmarket, and how to transition from SMB to enterprise. Another really great interview with David Katz, Senior Sales Director at Intercom. What You’ll Learn.

SMB 71

SMB Enterprise Scale VP of Engineering 71

SaaStr

DECEMBER 1, 2023

We’re still learning what world we’re in — some people interview over Zoom, some are focused on how to build teams in the current age, and many are dealing with a weird overhang from the SaaS explosion of 2021, quiet quitting, layoffs, and team turnover. But they might want to stick with SMB. There’s no way.

Sales Hiring 159

Sales Hiring Sales Recruiting Sales Interviewing 159

OpenView Labs

JANUARY 31, 2022

Do they understand your GTM motion (enterprise vs mid-market/SMB)? Make a clear plan for your interview process . A strong interview process plan goes deeper than simply who candidates will interview with. . Each round or step of the process and interviewers in each. Have they built teams? EST / 9 a.m.

Sales Hiring 60

Sales Hiring Interviewing Sales Recruiting SMB 60

SaaStr

SEPTEMBER 26, 2019

So up to 100-150K and SMB, we’re at 2K. Gaetan Gachet : I think we stopped doing that maybe six months ago, but we still have engineers who interview sales people, sales candidate. We interview on values during our recruiting process. Gaetan Gachet : So during the interview process, all the interview process is in English.

Scale 148

Scale Sales Hiring Sales Recruiting Technical Advisors 148

Sales Hacker

OCTOBER 30, 2019

How do I get promoted from SMB/MM to enterprise? When one LoB closes… How Do I Get Promoted from SMB/MM to Enterprise? My favorite interview question for anyone who has been successful in their sales career is, “Congratulations! The post Selling to Enterprise (Just Like Selling to SMB… Right?) HOW did you do it?”.

SMB 53

SMB Enterprise Technical Review Interviewing 53

SaaStr

JULY 2, 2019

Dannie : They call them, they engage with them, and then they end up having a user interview where they figure out what hurts, what drove them to Slack, what feels good about using Slack, and what could we do to help them as they think about collaborating even more smoothly across their whole org. We saw a really wide array of examples there.

Enterprise 170

Enterprise Scale Sales Hiring SMB 170

Sales Hacker

JUNE 20, 2018

I’ve got a very special interview today. They brought me in to interview and I literally had to speak with Diane Greene and convince her that I could be a great sales rep for her team. They had a small SDR team—primarily Inbound and an SMB sales team. About Jaimie Buss and Zendesk: Baseball Card Stats. Sam’s Corner.

Scale 99

Scale Sales Hiring SMB Interviewing 99

Intercom, Inc.

OCTOBER 29, 2019

Sales: Be able to route prospects to our self-service flow or the most appropriate team within Sales, e.g. startups, SMB, MME, based on well-defined customer segments. Our initial efforts resulted in this matrix: To further validate our model, we interviewed representative customers in segments that were new to us as a business.

Business 184

Business B2C Scale Headcount 184

Sales Hacker

NOVEMBER 9, 2020

Having the right technology in place is often the difference between success and failure, and this is even more true for startups and SMB, where you have a small team and limited resources. This isn’t the only effect WFH has had on the sales tech market, though.

Technical Review 133

Technical Review Scale Trends Startup 133

SaaStr

JULY 24, 2019

Final point about Talkdesk is that we started selling about five years ago in the SMB space. These may feel a little soft, but they’re incredibly helpful in the hiring process, because probably like many of you, I spend a lot of my time on video conferencing, interviewing candidates.

Retention 162

Retention VP of Engineering Sales Hiring Scale 162

Payrix

JUNE 25, 2024

Understanding the hype around Embedded Finance The excitement around Embedded Finance is driven by several underlying dynamics in the SMB (small and medium-sized businesses) market. In recent years, SMBs have increasingly adopted vertical-specific software to run their businesses. Leah Asdell Hi everyone.

Payments 100

Payments Payment Solutions Finance Embedded Payments 100

Intercom, Inc.

OCTOBER 22, 2019

As a manager, the tasks competing for your attention only multiplies – coaching , training, interviewing, forecasting , planning, and more. But if you want to succeed, you need to focus on moving fast where it matters. For LB, this means having a consistent, well-defined rallying cry for her team to get behind.

Sales Hiring 123

Sales Hiring Underperforming Technical Team Sales Management 123

Sales Hacker

JUNE 27, 2019

That’s why one of the most important things you can do is to make sure you’ve firmly established your vision and mission — and can articulate it in a compelling way during interviews (including examples of how to back it up). There is a big difference between selling to the SMB, Mid, and Enterprise markets. This will act as a magnet.

Sales Hiring 72

Sales Hiring Sales Recruiting Scale Outsourcing Services 72

Sales Hacker

FEBRUARY 13, 2020

When you are selling to SMB and MM, you can get away with fairly lean marketing. RELATED: From SMB to Enterprise: A 2-Step Strategy to Boost Adoption & Growth. Make no mistake, this is a long way from the SMB sales motion! You never asked that in SMB did you? Customer and channel partnerships. Sales strategy.

Sales Hiring 90

Sales Hiring Enterprise Technical Review SMB 90

Intercom, Inc.

MAY 13, 2021

You can also read the full transcript of the interview, which has been lightly edited for clarity, below. Of course, we always excelled in SMB at Slack as well. It’s not analogous, but there are learnings you can take in your SMB business as you think about going up or getting into bigger companies and bigger deployments.

Scale 177

Scale Customer Success Sales Hiring Strategy 177

Intercom, Inc.

JUNE 21, 2018

There’s not really a lot of SMB, which is more like growth hacking rather than breaking into bigger deals. I think the actual hiring process is the best you’re ever going to see of the person you’re interviewing, so that’s kind of a sales process right there. A lot of my advising is actually around hiring.

Sales Hiring 183

Sales Hiring Scale Sales Recruiting Technical Advisors 183