SaaStr

JULY 27, 2022

If a SaaS business hopes to win over the SMB market successfully, it will need a precise GTM approach. Founded in 2015, PayFit is a software company that empowers entrepreneurs and SMBs to digitize payroll and HR processes. Without an autonomous-first approach, you will miss out on many SMBs.

SMB 244

SMB Sales Hiring Scale B2C 244

SaaStr

OCTOBER 6, 2024

Loren has been a SaaS SMB+ leader for years, running Shopify Plus and revenue leadership roles at Bill and Podium as well. Mass email campaigns haven’t worked for them, no have they for other vertical SaaS SMB leaders I’ve invested in. Selling to Small Business Owners is Hard.

Sales Hiring 272

Sales Hiring SMB SaaS Leadership 272

SaaStr

MARCH 25, 2021

Having said that, the average ACV here is $14,615 … so that’s at the high end of a traditional SMB spend, which probably accounts for the high NRR. While Shopify and BigCommerce pricing isn’t identical in the end, their SMB / published pricing is almost identical. Not competing (directly) on price.

Outsourcing Services 289

Outsourcing Services Payments Merchant Services SaaS Payments 289

SaaStr

JUNE 7, 2023

It has now secured over $67M in funding and offers a robust platform for mid-market and SMB segments. But the drive and passion remained, and leadership didn’t give up. WorkRamp shifted its focus to a different segment –– the mid-market and SMB side. Customer Impact : A much better PMF for SMB & Mid-Market customers. “You

Scale 246

Scale Scaling SMB Marketing 246

SaaStr

MARCH 22, 2024

After switching to SaaS, she started as an SMB sales leader with no prior management or SMB sales experience. She was able to get into a leadership position immediately and coach people who were hungry for it in a slightly safer space than more tenured folks.

Scale 300

Scale Underperforming Technical Team SMB Finance 300

SaaStr

APRIL 8, 2023

Here’s a list of some of the most popular to dig into: Atlassian’s CRO Cameron Deatsch: “How The Biggest Product-Led Enterprise Company In The World Did It” Skilljar’s CRO: “An Inside View on Hiring Your First CRO” Rippling’s CRO: “Entering a Hyper-Competitive Market” DigitalOcean’s (..)

Scale 300

Scale Sales Hiring SMB SaaS 300

SaaStr

JANUARY 21, 2020

It’s an SMB SaaS company in the healthcare technology vertical. My velocity lane, PatientPop’s SMB SaaS, eight units a month, $13,500 contract. If you’re an SMB SaaS business, I would recommend hiring SMB SaaS salespeople. Hey everyone, is this thing on. Hey everyone. My name is Justin Welsh.

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

SaaStr

MAY 21, 2021

But Box became 95%+ enterprise by revenue over time, and Dropbox is still 95% SMB and smaller and consumer. But — Dropbox is much more of a consumer and SMB focused product. Let’s contrast Box and Dropbox. Both grew into huge wins and highly successful public companies. Less TV, far fewer events, no big customer conference, etc.

Enterprise 339

Enterprise SMB Scaling Revenue 339

SaaStr

FEBRUARY 14, 2024

You Mon Tsang, CEO and co-founder of ChurnZero, Colleen O’Sullivan, VP of Integrated Customer Experience at Hubspot, and Jason Lemkin, SaaStr founder and CEO, give their take on where the customer success industry is headed and shares data from the Customer Success Leadership Study done by ChurnZero at the close of 2023.

Customer Success 299

Customer Success Sales Hiring Scale Headcount 299

SaaStr

MAY 23, 2023

Enterprise Quota:OTE ratios are higher (5x+), SMB is a bit lower, but at the end of the day, you need to close 4x-5x what you take home. #2. Sales Leadership Typically Has 40% or So From Variable Comp. Yes, 50/50 Base/Variable for AEs remains the standard, and 4x-5x+ Quote:OTE ratio remains the standard. CSMs Are Pushing Up to 20%.

Compensation 301

Compensation Scale Sales SMB 301

Tom Tunguz

AUGUST 2, 2016

Channel distribution represents one of the biggest and most important changes in customers acquisition for SMB SaaS startups in quite a while. One of the most interesting examples is Microsoft’s Office 365 SMB business. It’s the most successful SMB SaaS acquisition channel ever built. by Thomas Hansen.

Outsourcing Services 110

Outsourcing Services SMB Acquisition Scale 110

SaaStr

DECEMBER 1, 2021

Mark spent 10 years at Salesforce where he held a variety of sales leadership roles, including senior vice president of Marketing Cloud, senior vice president of global sales for Salesforce Pardot, and senior vice president of commercial sal es. Mark Waylan is the Chief Revenue Officer at Box. ” Sid Sijbrandij, CEO @ Gitlab.

Scale 278

Scale Scaling SMB compliance 278

SaaStr

MARCH 3, 2023

A scalable buddy system allows people to learn coaching and leadership skills. Don’t discount empathetic leadership. For SMB mid-market, it’s typically around 2-3 months. To avoid this snag, set up a buddy system where you pair more tenured salespeople with new hires, helping to support, enable, and train them.

Scale 273

Scale Sales Recruiting Sales Hiring Scaling 273

SaaStr

OCTOBER 3, 2023

Finding product market fit Moving from SMB to Enterprise or vice versa Achieving Enterprise repeatability Strategic expansion Borland has experienced all four stages at three different companies and knows what teams and functions look like for each stage of growth. Through customer stories.

Enterprise 291

Enterprise B2B Scale SMB 291

SaaStr

JUNE 20, 2023

I’m basically an SMB these days. Subscribed Dear SaaStr: What are some good questions to ask a CEO in regards to their leadership? I lose patience here and move to a vendor I can just deploy without being forced to talk to an SDR that just wants to force me to get on the phone and screen me but doesn’t get me going now.

Sales Hiring 268

Sales Hiring Scale Sales SMB 268

SaaStr

JULY 22, 2022

Koehler emphasized the similarity in pain points across multiple customer segments: “It doesn’t matter if you’re an SMB…or a large enterprise: You’re trying to figure out, ‘How do I create a better customer experience? How do I engage my customers? And quite frankly, how do I make my employees collaborate in a world that is very hybrid?’

B2C 283

B2C Scale Marketing Sales Hiring 283

SaaStr

DECEMBER 27, 2023

They started via SMB and are now serving the Amazons of the world. The more SMB you are, the faster the sales cycle and the quicker the team learns. Leadership injections as you scale are tricky. Over time, they realized the product value was best spent with high-complexity organizations.

Sales Hiring 277

Sales Hiring Scale SMB Outsourced Development 277

SaaStr

SEPTEMBER 15, 2023

Big Bet #4: Go After Bigger Fish — Overlay Field Motion Over Inbound People often assume inbound is all SMB, but one of the things Freshworks realized early on is that you can close larger deals with inbound. The average SMB customer would buy 4-5 seats of Freshdesk. Inbound isn’t just about SMB customers. The lesson?

Sales Hiring 284

Sales Hiring Scale SMB AI 284

SaaStr

JULY 1, 2024

Right now, you may have 3-4-stage sales processes that work for SMB customers. Hopefully, you’ve built a partnership ecosystem for SMB customers, but it’s probably a completely different strategy for what you need to go upmarket for a couple of reasons. So, find sellers inside your sales org who can at least get you started.

Sales Hiring 300

Sales Hiring Scale SMB compliance 300

SaaStr

JULY 24, 2024

The best leadership finds a way even in slightly tougher times. Another issue is when a CEO doesn’t know what to do, especially in a high-churn model like SMB. The best leaders find a way. Is it easy to hire mercenary VPs when you’re growing 500%, or you’ve raised $100M? One thousand folks want to join you and think you’re great.

Sales Hiring 301

Sales Hiring Startup Scale SMB 301

SaaStr

JUNE 22, 2023

SMB folks want to go upmarket because there is too much churn in SMB. . – SaaStr Trying to pursue a “Grass is Greener” business model. Enterprise folks want to do freemium because they think it is easier. B2B folks want to do B2C. That’s OK, but pretty risky. 85 times out of 100 — do what you know. If you can close $1m deals — do that.

SMB 274

SMB SaaS B2C Interviewing 274

SaaStr

NOVEMBER 18, 2020

Don’t go upmarket if you purely, 95-100% an SMB product. As CEO and founders, your job isn’t to meddle in what your VPs and leadership team already know how to do. This isn’t to say all apps should go enterprise. If you can get to $5m, $10m, $20m+ with a freemium or self-serviced product, do that by all means.

Sales Hiring 363

Sales Hiring Scale SaaS Enterprise 363

SaaStr

SEPTEMBER 22, 2022

Chestnut states that the weirdness has a point –– to stand out and reach marketers and SMB owners: “The first couple of iterations of our brand were a little bit weird and funny in a ‘monkey’ kind of way…[the customers] just loved it, and we just sort of rolled from there.”

SMB 256

SMB Entertainment Acquisition Branding 256

SaaStr

MAY 5, 2022

In the same way, the focus of sales leadership will become more tantamount as organizations grow. And with even more scale, determining whether to sell upstream (enterprise) or downstream (SMB) might prove challenging. Principle #4: At Scale, Focus is Critical. Every time we’ve focused and made a hard tradeoff, we’ve succeeded.”.

Scale 246

Scale Sales Hiring Scaling Sales 246

SaaStr

JUNE 13, 2019

And they were broken down roughly a third, a third, a third by targeting the SMB, the mid-market, and the enterprise. In the SMB, two-thirds use month-to-month, and in the enterprise, you’ve got two-thirds using multi-year. In terms of ACV, they span the gamut, everywhere from 5K all the way to 150K plus. What does this mean?

Scale 252

Scale SMB Sales Hiring Payment Services 252

SaaStr

DECEMBER 21, 2022

But leadership at Airtable saw themselves moving into the overall agile workspace years down the road and chose their competitors based on that goal. It takes a lot of intentional investment to scale with enterprise customers in addition to self-serve or SMB markets.

Scale 245

Scale Enterprise Scaling Management 245

SaaStr

NOVEMBER 16, 2021

Positions Needed: Enterprise AEs, Mid-Market & SMB AEs, SDRs, Sales Ops, Sales Engineer. Positions Needed: Enterprise CSM, Mid-Market & SMB CSM, Customer Support Reps, Implementation/Solutions Engineer. Head of Marketing. Team Size: 5 – 6. Director of CSM. Team Size: 4 – 8.

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

MARCH 19, 2021

No VPS can be great at inbound, outbound, field, SMB, Enterprise, Channel Partners, Strategic Accounts, High Velocity Sales. Someone that can’t possibly help the VP who hasn’t done it her himself. Net net, no VP can do it all. Especially when most of you are hiring Stretch VPs in your first management team.

Sales Recruiting 349

Sales Recruiting Sales Hiring SMB Engineering 349

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 125

Sales Recruiting SMB Scale Sales Hiring 125

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. Moving from enterprise sales leadership to a startup environment. Discussed in this Episode: How to turn coworkers into mentorsand why it matters.

Scale 68

Scale Sales Hiring Scaling Revenue 68

SaaStr

JUNE 27, 2019

When we were SMB focused in the early years, our sales cycles were quick. Product org changes quite a bit as well and as one chief product officer shared with me, he said, “You know, when we made the transition from SMB to enterprise, we went from being kind of in control of our own destiny and certainly of our own time.

Scale 238

Scale Enterprise Scaling Sales Hiring 238

SaaStr

SEPTEMBER 11, 2023

4: Too Much — or Too Little — Outside DNA If you hire everyone from outside the company to your leadership and senior teams, you lose what makes you special. And certainly, there are categories that are very SMB, so going too upmarket too early doesn’t make sense. Because the vast majority of the revenue is in SMBs.

Sales Hiring 312

Sales Hiring Scale Sales Recruiting Scaling 312

Totango

APRIL 1, 2021

Totango is excited to announce that we have once again been recognized by G2 with awards for our leadership in Customer Success. The post Totango Earns Multiple Leadership Awards from G2 appeared first on Best Customer Success Blog | Trends & Articles for Enterprise Growth. Try Totango For Yourself.

Leadership 84

Leadership Systems Review Software Review SMB 84

Sales Hacker

SEPTEMBER 25, 2019

Enterprise sales is hard, which is why most businesses start as an SMB org and grow into an enterprise org. And those that do often struggle through the transition, leaving behind a churn of leadership and sales resources after every funding milestone. 2 rules for transitioning from SMB to enterprise. That’s not hard to believe.

SMB 88

SMB Enterprise Strategy Compensation 88

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 111

Sales Recruiting SMB Scale Sales Hiring 111

OpenView Labs

JANUARY 12, 2022

It might be a little surprising to learn that the leadership style at Stack Overflow is decidedly not binary. Step 2: Adopt a flexible, non-dual approach to leadership. Prashanth takes a different approach for himself and the leadership style at Stack Overflow. Step 3: See what happens when you forge your own path.

Leadership 76

Leadership SMB Underperforming Technical Team Scale 76

SaaStr

NOVEMBER 19, 2020

But a great head of demand gen (or maybe growth hacking if you are SMB) should be very accretive at even $20k in MRR. The chart above illustrates the ideal plan, but let’s dig into the detailed suggestions: You really can and should try to hire your VP of Marketing as Early as $20k in MRR. This will seem crazy early to many of you.

Part-Time VPE 363

Part-Time VPE Sales Hiring CTO Hire Scale 363