SaaStr

MAY 24, 2025

Top 10 Strategies Toasts CRO Uses to Crush Sales Quotas So a little while ago Toasts CRO Jonathan Vassil joined Sam Blond on SaaStr CRO Confidential on how Toast built one of the strongest but toughest rocketship in sales: a lower gross margin, lower ACV ($10k), sales-led SMB sales motion. Even with SMB Sales. Field-Based Sales Model.

Strategy 144

Strategy Payment Solutions Payment Methods SMB 144

SaaStr

FEBRUARY 8, 2022

Waze sales executives Fernando Belfort , Head of SMB Sales, and Kendra Wrightson , Head of Sales Enablement, discuss optimizing sales processes for four essential data points: value, variety, volume, and velocity. You’re not the only SMB asking this question as you navigate perpetual pitches, closing clients, and growth. .

Scale 297

Scale Sales Hiring Compensation Sales 297

SaaStr

JANUARY 21, 2020

It’s an SMB SaaS company in the healthcare technology vertical. We’re going to move into things like learning and development, L&D, building on great career pathing and getting that compensation right and I’ll give you a preview. If you’re an SMB SaaS business, I would recommend hiring SMB SaaS salespeople.

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

Tom Tunguz

APRIL 8, 2015

There’s a familiar path now to SaaS companies that start in the SMB (small-to-medium business) part of the market. In short, new startups leverage a distribution advantage to acquire SMB customers at scale. SMB 3-7% 31%-58%. SMB customers tend to go out of business more frequently than bigger businesses.

Innovation 209

Innovation Startup Scale SMB 209

SaaStr

NOVEMBER 9, 2019

Expect much higher compensation / OTE in general, and often a large draw until their first deal closes. SMB sales: Reps generally are given 100+ leads a month from marketing / demand gen. Generally need to close 8–12 deals a month for larger SMB deals , more for small deals (>10x more than an enterprise rep).

Sales Hiring 191

Sales Hiring Enterprise Sales SMB 191

SaaStr

OCTOBER 4, 2023

Then everyone in the world was on Zoom selling flowers and yoga and things meant to be sold in person, so churn peaked at 3.6%, which isn’t terrible for SMB, but was higher than none. We’ve gotten used to certain types of sales compensation, certain levels of Customer Success, and certain types of coverage and marketing spend.

Sales Hiring 289

Sales Hiring SaaS Headcount Compensation 289

Sales Hacker

AUGUST 29, 2023

And…monthly bonus podcast episodes dropping the first Thursday of every month The post GTM 58: How Stripe SuperCharged their SMB Team with Meka Asonye appeared first on GTMnow.

SMB 94

SMB Scale Compensation Sales Hiring 94

SaaStr

OCTOBER 26, 2023

In a year like this, SMB is doing worse, with a lot more churn and startups going out of business. But in other years, SMBs are jumping in the boat, so you get amazing growth long-term with a multi-segment strategy. But in other years, SMBs are jumping in the boat, so you get amazing growth long-term with a multi-segment strategy.

Sales Hiring 286

Sales Hiring AI SMB Scale 286

SaaStr

APRIL 13, 2022

Think about an SMB rep doing small-but-not-tiny deals — say $2k ACV. Maybe 3–4 demos max for deals in process a day. And each might take an hour with prep, more if enterprise. And that doesn’t leave 2 hours a day for follow-up, admin, etc. They’d have to close 25 deals a month to hit their OTE. That means every deal they have to close 1 deal.

Sales 319

Sales SMB Enterprise SaaS 319

Sales Hacker

DECEMBER 12, 2017

With increasing focus on grit and many claims of meritocracies in organizations across the country, why does variable pay compensation even exist? On top of that, why are sales people some of the few employees subject to variable compensation structures? What is Variable Pay Compensation Anyway?

Compensation 98

Compensation Sales Hiring Sales Payment Services 98

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. So let’s look at how to drive sales in a high-growth situation, so the transition from SMB to enterprise is smoother (and faster). 2 rules for transitioning from SMB to enterprise. Align compensation for long-term goals.

SMB 86

SMB Enterprise Strategy Compensation 86

Sales Hacker

AUGUST 26, 2021

That’s how my friend Stacey describes the way sales compensation plans have changed over the last 15 years of her SaaS career. Why do sales compensation plans have to be so complex? Sales compensation was set up to ensure that reps are suitably rewarded for their performance. Ramp policy. What is their policy on draws?

Software Review 120

Software Review Compensation Payment Features Underperforming Technical Team 120

Sales Hacker

APRIL 10, 2018

The SMB segment—going upstream vs. downstream. Pro-user, SMB, Enterprise, this requires a specific Go To Market strategy. SMB/Group like – selling applications using an annual/monthly/usage contract. The SMB Segment: Going Upstream vs. Downstream. The importance of the SMB segment.

SMB 95

SMB Strategy Outsourced Development Marketing 95

SaaStr

MARCH 31, 2022

So I think just opening your aperture when you’re thinking about marketplace, not assuming it’s just a small commercial SMB market sales. And I would also say, regardless of the field, is how you go about compensating this channel. Actually we were, I would say pleasantly pulled there by a lot of our enterprise customers.

Scale 262

Scale Marketplace as a Service Cloud SaaS Payments 262

SaaStr

OCTOBER 29, 2019

SaaS is about creating long-term value for your customer, and being compensated appropriately for that value as a business. This is a mobile solution for SMB’s to send an invoice and get paid. There’s a client of Simon Kutcher’s that caters to the SMB segment and they weren’t happy with their revenue growth.

Payments 111

Payments Pricing Compensation Scale 111

ChurnZero

DECEMBER 2, 2021

From sessions on building variable compensation plans and Customer Success tech stacks to fostering customer advocacy and community, BIG RYG explored how today’s Customer Success leaders are tackling major industry challenges and advancing their Customer Success game. Variable compensation plans need to be achievable.

Customer Success 98

Customer Success Technical Review Scale Compensation 98

Sales Hacker

AUGUST 7, 2020

The plus side of this is that it leads to a comradery at start-ups and SMB organizations that is often hard to replicate at the enterprise level. Salespeople are not as tightly managed in start-ups or SMBs, and most of us like that. There are thousands of very successful SMB companies that offer lucrative sales careers.

Scale 104

Scale Enterprise Sales Hiring Technical Review 104

Sales Hacker

OCTOBER 9, 2019

In many SMB companies, the business owner wears many hats, one of which happens to be the sales manager. I was compensated based on the team’s performance, with the opportunity to earn a higher income as a successful manager than I could previously as a successful sales representative. Compensation. Aptitude for management.

Sales Hiring 90

Sales Hiring Leadership Sales Management 90

SaaStr

JUNE 16, 2020

It’s available to everyone bringing in third party speakers, bringing in, we had Mark Cuban couple of weeks ago, we’re having Brene Brown for our SMB business, around empathy, and leading through courage. It’s the SMB space. And so Leading Through Change is a series we’ve launched. One, Salesforce Care.

Sales Hiring 210

Sales Hiring Scale SaaS Payments Payment Services 210

SaaStr

JULY 24, 2019

Final point about Talkdesk is that we started selling about five years ago in the SMB space. One thing that we have implemented is every time a customer turns now, and I realized this is not scalable if you’re in the SMB space and you have 50000 customers; but for Talkdesk with 1500, any time a customer turns, we do a full postmortem.

Retention 161

Retention VP of Engineering Sales Hiring Scale 161

Sales Hacker

JUNE 20, 2018

They had a small SDR team—primarily Inbound and an SMB sales team. Here’s the tactical part—Jaimie compensates her Inside Sales team for both the self-service leads and SMB leads. Sam Jacobs: What was Zendesk’s Sales organization like when you inherited it? And, what does it look like now? Don’t Miss Episode 13.

Scale 98

Scale Sales Hiring SMB Interviewing 98

Sales Hacker

JUNE 14, 2018

Perhaps you are expanding into the SMB space and have not been able to gain a measurable return. Can you illustrate your firm’s proven track record of selling in the enterprise, mid-market, or SMB segments ? If you need expertise in selling to the SMB space, do they have current teams actually selling to SMBs?

Outsourcing Services 79

Outsourcing Services Sales Hiring Sales Outsourcing Outsourced Development 79

SaaStr

SEPTEMBER 26, 2019

So up to 100-150K and SMB, we’re at 2K. The next stage was we hired more junior people who would do the first call and work on SMB accounts and we would have the more senior work on mid-market and enterprise accounts. So we had SMB, mid-market and enterprise. Gaetan Gachet : Depends on the segment. for enterprise.

Scale 150

Scale Sales Hiring Sales Recruiting Technical Advisors 150

Sales Hacker

APRIL 1, 2025

The exact playbook to move from SMB to enterpriseincluding partner enablement, segmentation, and incentive design. 85% of your customers being SMB and mid-market to at the end of that six years, it was 75%, uh, enterprise. Why retention isn’t just a CS metricand how to build a sales team that cares about it.

Scale 63

Scale VP of Engineering Outsourcing Services Enterprise 63

SaaStr

JULY 1, 2020

Then, we’ll end of the day with me and Stewart Butterfield and obviously Slack is doing well, but Slack also has a massive SMB base and its challenges. For example, we’ve got like Roman from Gorgeous that Sam knows at the end of the day talking about dealing with SMB turns, they did something interesting at Gorgeous.

Merchant Services 263

Merchant Services Scale Sales Recruiting Sales 263

Sales Hacker

OCTOBER 30, 2018

She helps SMB companies drive growth by incorporating the newest research and best practices to enable business owners to bring about sustainable change that leads to growth. She is adept at managing SMB, MM, and Enterprise sales coverage models, quota setting, and compensation plan design.

Sales Recruiting 111

Sales Recruiting VP of Engineering Scale Sales Hiring 111

OpenView Labs

FEBRUARY 3, 2022

Simpler segmentation approach : By bucking the good, better, best seat-based pricing model, a single price point can be used to satisfy cost-conscious SMB customers as well as mid-market/enterprise businesses. In 2021, we saw that fast growers were nearly 3x as likely to use a largely usage-based pricing model versus slow-growing peers.

Headcount 73

Headcount SaaS Compensation Acquisition 73

Sales Hacker

JANUARY 29, 2018

Reps were hired, trained and compensated to perform as an individual to hit a quota. To grow, the company needs to structure its resources into two initiatives; SMB and MidMarket, each requiring a different approach. The Winning By Design Blueprint Series provides practical advice for every part of a SaaS sales organization.

Sales Recruiting 91

Sales Recruiting Scale Sales Hiring Sales 91

Intercom, Inc.

JANUARY 11, 2023

People are going to ask for more data to compensate for some of the inaccuracies, and then, you just create more and more friction. Liam: The third learning was that product usage skews towards SMB. Everyone feels good about it and wants to do it, but at the end of the day, unfortunately, it’s just not that valuable.

Scale 118

Scale B2B Banking SMB 118

InsightSquared

MAY 22, 2019

In the mid-market and SMB worlds, we can create an activity focused and pipeline coverage oriented ‘reverse engineering’ approach to figure out where we are going to land. Compensating the Troops. Bid management: When responding to enterprise tenders, a structured process to coordinate strategy and resources is required.

Sales Hiring 94

Sales Hiring Enterprise Engineering Outsourcing Services 94

SaaStr

AUGUST 12, 2020

We had SMB mid-market and enterprise teams, so we were attacking all those markets. Some of the TCV numbers might’ve included multi or deals, but we basically went from one million in sales our first full year as a company, to seven million the second, to 21, to about 56 million the year that Microsoft bought us.

Startup 299

Startup Software Review Scale Systems Review 299

Sales Hacker

SEPTEMBER 16, 2019

Compensation. Inside sales focuses on SMB, mid-market buyers. Compensation. RELATED: How to Build Effective Sales Compensation Plans for Any Customer Facing Role [Templates]. How can inside and outside sales work together? Hiring guide. Skills and qualifications necessary for inside sales. What Is Inside Sales?

Sales Hiring 97

Sales Hiring Scale Sales Recruiting Payment Methods 97

Sales Hacker

APRIL 29, 2021

If they are reps, and are consequently rewarded for hitting quota and using time to make dials, be sure they have recognition or compensation set aside for these new responsibilities (i.e. Our friends in SMBs may have been in the sales realm for a while, with reps who are used to doing their own things.

Scale 116

Scale Sales Hiring Sales Headcount 116

Kellblog

FEBRUARY 8, 2021

SMB oppties tend to move faster than enterprise ones. Focus on finding new opportunities that move fast. Remember that nine-month sales cycle is an average; s ome opportunities close a lot faster. Expansion oppties tend to move a lot faster than new logo oppties.

Systems Review 98

Systems Review Software Review Forecasting Advertising 98

OPEXEngine

JANUARY 11, 2022

Companies that do not need to lock customers in with minimum commitments, particularly in the SMB space, use these types of models. Pay for performance compensation plan. Sales compensation. Align the sales compensation plan to the seller’s role and tie the incentive as close as possible to the multiple persuasion event(s).

Pricing 52

Pricing Payment Solutions Outsourced Development Compensation 52

ChurnZero

JUNE 11, 2021

Another example is creating a health score based on tiered implementation: SMB onboarding versus Enterprise onboarding. Explore weighting factors differently for greater insight into a specific product or service. . How to Measure the Effectiveness of Customer Health Scores.

Software Review 96

Software Review Systems Review Underperforming Technical Team Scale 96

Sales Hacker

NOVEMBER 15, 2017

Base Salary refers to an agreed-upon amount of payment an employee received as compensation for work rendered. A bonus is a gift or additional compensation given on top of the standard pay or fee, often serving as a reward for outstanding performance or for achieving certain business targets. Compensation. Channel Partner.

Scale 105

Scale Payment Methods Sales Recruiting SaaS Payments 105