SaaStr

AUGUST 9, 2024

From startup to $500M CARR, Spencer Burke, SVP of Growth at Braze, shares how Braze scaled a growth and customer success team. In this AI moment we’re in, there are still many moments in scaling a company where intuition still matters. You don’t have to leave as the organization scales. This isn’t new.

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Scale Sales Hiring Scaling Startup 291

SaaStr

FEBRUARY 12, 2025

Meet Wyatt Jenkins: From Construction Sites to Chief Product Officer If you want to understand how vertical SaaS companies scale to $1B+ in revenue while staying true to their customers, there’s no better person to learn from than Wyatt Jenkins, Chief Product Officer at Procore Technologies.

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Construction Scale SaaS Travel 251

SaaStr

FEBRUARY 7, 2025

Speaker Bio Jason Lyman leads marketing at Customer.io, where he’s helped scale the platform to power over 35 billion customer interactions for 7,000+ high-growth companies. Before Customer.io, Jason built and scaled marketing teams at several B2B SaaS companies, with a focus on customer engagement and revenue operations. .

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Scale SaaS B2B Scaling 271

SaaStr

JULY 11, 2024

There’s only a small chance that it’ll be an IPO exit, and Stacey Bishop with Scale Ventures shares what it takes to get to that next level of funding. But that shifts over time, and most of your spend goes into sales and marketing. The 3 Other Vital Signs Investors Look For Sales efficiency becomes more important over time.

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Scale Scaling Churn Investment 300

FastSpring

JANUARY 23, 2025

Listen for the full insights into: How Flippa.com works to connect for-sale businesses with buyers while managing the complexities of valuation and seller expectations. When I was running it, it was a lot smaller than that, but scaled that up very, very quickly. And that’s substantial scale in.

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Scale Entrepreneurship Scaling Underperforming Technical Team 119

SaaStr

MARCH 1, 2024

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders? You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. You will need a VP of Product to scale your roadmap. But you won’t scale past $4m-$5m without a true, seasoned VP of Engineering. As are you.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

SaaStr

AUGUST 5, 2024

When you find the answer to these questions, you can expand an existing customer base and create cool data-driven case studies to help your sales team bring in net business. 1: Build a Value Narrative Value narratives have been around for some time in pre-sales motions. Often, that doesn’t feed through to post-sales.

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Scale Customer Success Scaling Revenue 284

SaaStr

JANUARY 24, 2024

Mark Roberge , SaaStr fan-favorite and Co-Founder and Managing Director of Stage 2 Capital brought together some of the top CROs in SaaS during the SaaStr Annual to share some of their greatest learnings and pivotal moments leading some of the Cloud 100 SaaS companies. How do you diagnose and solve churn?

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Scale Sales Hiring Scaling Revenue 273

SaaStr

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? Ways to scale that don’t include rampant inefficiency and burn. Early churn was a massive drag on efficiency. They needed to get their hands on early churn. This led to fairly unsustainable levels of churn of early churn.

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Scale SMB Sales Hiring Sales 301

SaaStr

NOVEMBER 28, 2024

It’s just hard to get most vertical SaaS start-ups to scale if they can’t get to a $10k ACV. The good news is, you can support these price points effectively with a very efficient inbound sales team, and/or a mix of self-serve and sales-led. Churn is all over the place with SMBs. So be honest.

Payment Solutions 261

Payment Solutions Inbound Sales Team Marketing Scale 261

SaaStr

JUNE 22, 2021

This is a positive trajectory, but it presents a challenge for your customer success efforts: How can you scale your support and CS while still delivering a memorable, quality customer experience? According to the Totango report, 77% of respondents said that scale was their top challenge. Key Takeaways For Scaling Growth.

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Scale Customer Success Scaling Compensation 278

SaaStr

DECEMBER 30, 2020

There’s a set of questions I get asked all the time: Should you pay sales reps on renewals? Should you pay sales reps on upsells a long time down the road? Should you pay sales reps on … ? I am a huge proponent of paying sales professionals well. You need to, to scale in SaaS. for the sales team.

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Scale Sales Hiring Sales Churn 311

SaaStr

FEBRUARY 11, 2021

In SaaS, #1 most common misfire, with a bullet, is the VP/head of sales. It goes something like “You’ve Got to Get Past the Carcass of Your First VP of Sales” or “It’s The Second VP of Sales When You Really Start Selling” or variants thereof. Because in SaaS start-ups, it seems like the majority of first VP Sales fail.

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Sales Hiring Scale Sales Recruiting Sales 363

SaaStr

JANUARY 5, 2022

Companies that spend $500k with us in their first contract may or may not churn down the road, but companies that slowly increase their spend year over year are much more likely to stay with you in the long run, ultimately bringing you more revenue. Improvements for a sales team and process are a ‘no finish line’ business.

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Scale Scaling Sales Hiring Software Review 301

SaaStr

DECEMBER 2, 2020

My 7 top tips to increase sales quickly. Hire a great VP of Sales. Hire a great VP of Sales, and even if nothing else changes … she’ll increase the revenue per lead by 20–100%+. In one sales cycle or less. More here: How My VP, Sales Doubled Our Sales in 90 Days. Leads are precious.

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Scale Sales Hiring Sales B2C 317

SaaStr

JULY 29, 2022

Jason recently opened up an AMA on Twitter Spaces to answer questions about how to scale faster. And I’ve watched them fairly quickly scale, to soon they’ll be at 10 million in revenue. As they scaled, they radically changed how they did sales. Jason Lemkin: Okay. Let’s get it going. Times are good.

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Scale Scaling Sales Hiring Enterprise 273

SaaStr

FEBRUARY 16, 2021

Q: What are the common mistakes in B2B sales in the early-ish days? The list could be endless, and it can vary a lot based on type of customer, type of sale, etc. The list could be endless, and it can vary a lot based on type of customer, type of sale, etc. Firing” prospects. Do not fire a prospect. A lot more.

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Scale Sales Hiring Sales SaaS 279

SaaStr

JUNE 13, 2022

And I’m going to suggest two that will worry you a lot as you scale — Churn and Sales Cycle — you should track, but not obsess over, until you are well, well past initial traction, that first $1m-$2m ARR. >> Let’s Start with Churn. Second, most SaaS product have an inherent rate of churn.

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Sales Hiring Scale Churn Metrics 274

SaaStr

FEBRUARY 15, 2022

E.g., Sales +Marketing Expenses < First Year ACV = Success ? But maybe not while you are scaling, you can often afford to invest more if you have funding. if Churn > 2% = Bad, Just Terrible. What most matters is that churn is going down , rather than the core absolute value, IMHO. Well — Maybe.

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Scale Customer Success Sales Hiring Scaling 261

SaaStr

SEPTEMBER 10, 2020

We’ve talked a lot over the years about how not to hire a wrong VP of Sales — 70%+ of the first VPs of Sales don’t make it even 10 months. And figure out if they really are great: For your prospective VP of Sales, did her top 2 hires at least crush it and blow out their quotas ? Drive up NPS and CSAT?

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Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 352

SaaStr

JULY 26, 2022

Don’t need as much sales experience on sales team. But beyond all the other Pros and Cons of SMB vs enterprise, there’s one looming issue with SMB SaaS: Churn. Endemic churn. The type of churn you almost can’t do anything about. And then 3% a month churn cuts your growth in half.

SMB 363

SMB Churn Payment Services SaaS 363

SaaStr

JULY 15, 2022

Jason recently opened up an AMA on Twitter Spaces to answer questions about scaling from $1M to $10M. We did a good AMA on this scaling at SaaStr Europa in Barcelona, a couple weeks back. That will scale, and then take those emails after four great pieces of content and do a weekly webinar and do a weekly get-together for them.

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Scale Outsourcing Services Sales Hiring VP of Engineering 293

SaaStr

FEBRUARY 15, 2021

There’s a slide I see again and again from start-ups: 2 of the early sales reps are at 100% of quota, sometimes 150%-200%. So why so often, do only 2 of the first 8-10 sales reps perform? The first 2 scaled reps you hire that hit plan (some may churn before then) get special training. And 8 others? And they fail.

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Scale CTO Hire Sales Hiring New CTO 348

SaaStr

OCTOBER 5, 2020

There’s a common thinking that sales teams should be relatively high churn. That the bottom 15-20% of the sales team almost has to churn each year, because it’s survival of the fittest. At Salesforce, at Box, the bottom end of the sales team churns out each year. They are routed leads.

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Scale Sales Hiring Sales Recruiting Sales 293

Intercom, Inc.

APRIL 6, 2022

With that in mind, the challenge businesses now face is striking the right balance between personalization and scale – which, historically, has been a tricky line to walk. Great experiences result in increased customer satisfaction, which often correlates to bottom-line results like reduced churn and increased retention.

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Scale Scaling DevOps as a Service Communication 230

SaaStr

APRIL 4, 2023

How CAC targets drive GTM strategies: If Your CAC Target Is Low You’ll likely focus on small-to-medium businesses and use tools like inbound sales and low-touch or no-touch self-service. The sales cycle at this stage may be very short. The sales cycle will be slightly longer at this stage. But over time, things change.

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Scale Scaling Strategy Outbound Sales Team 246

SaaStr

FEBRUARY 9, 2024

Everything from hiring on the GTM side to layering in a sales-led motion into PLG. Let’s dive into what’s making that hybrid model successful: PLG and Sales Led? Given this, you must understand the role that each facet of the business plays in promoting that product, from marketing and sales to customer service.

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Scale Sales Hiring Sales Marketing 317

SaaStr

MAY 23, 2023

So leading growth stage VC Iconiq has published its latest and very detailed Definitive Guide to Sales Compensation here. It’s very detailed and oriented more toward growth-stage scale-ups — but it’s excellent. Corners were cut in the boom times of 2021, but we are back to sane sales models.

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Compensation Scale Sales SMB 301

SaaStr

JULY 31, 2024

In this week’s Workshop Wednesday , SaaStr Founder and CEO Jason Lemkin shares the 7 things the best sales reps get right and the 8 ways the rest make things worse. #1: The best sales reps solve your problems. When you’re doing so well that you’re in order-taking mode, sales reps don’t have to solve a problem.

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Scale Sales Pricing ChatGPT 284

SaaStr

FEBRUARY 24, 2023

They initially double their ARR each year in scaling post $10M. Although churn and down-sell rates are relatively consistent during growth, this ability to capture new logos consistently can help to avoid client concentration in a volatile market. How do the best-in-class companies perform when ARR is treated as a growth metric?

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Scale Sales Hiring Scaling Venture Capital 246

SaaStr

FEBRUARY 28, 2022

A few ideas on how to help the sales team make this your best year so far: Hire dedicated sales / revenue ops. Many of you will have little to no dedicated help in sales operations , even up to $10m ARR or beyond. Getting routing the right leads? This will take some of the pressure off the sales team.

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Scale Sales Hiring Sales Enterprise 246

SaaStr

AUGUST 7, 2020

A few factors that contribute to high-performing sales teams: High quota attainment. The best startups invest in their sales teams and work hard so most of the reps hit and exceed quota. It does mean a well-oiled machine that hires strong reps of all backgrounds, and gets them the help and training so they can scale up and succeed.

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Sales Hiring Scale Sales Recruiting Compensation 363

SaaStr

SEPTEMBER 9, 2022

Back in the day, premium comp for some software sales execs made simple and easy sense. Traditional software had 90% gross margins, and the classic enterprise sales reps, the best ones, could close a million or more dollars a year. Sales reps in low NRR and high churn environments got paid almost the same as enterprise reps.

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Scale Venture Capital Sales Hiring Sales 345

SaaStr

NOVEMBER 21, 2020

How to hire a great VP of Sales (tons on that here ). What a great VP of sales really does. But as I now work with 24+ scaling SaaS companies, all of whom, all of us, who struggle to build a great management team … I’ve learned to distill it all down to one thing. About recruiting and helping you scale.

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Sales Hiring Scale Sales Recruiting Engineering 357

SaaStr

FEBRUARY 25, 2025

The Best Speakers In The World With hundreds of sessions from proven SaaS leaders who have scaled companies to significant revenue milestones, SaaStr Annual offers practical, actionable insights you won’t find elsewhere. Sessions typically focus on real metrics, strategies, and lessons learned, not theoretical concepts.

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Sales Recruiting Scale CTO Hire Sales Hiring 195

SaaStr

MARCH 9, 2025

Jess Clark, Head of User Experience at Calendly Jess leads Calendly’s user experience initiatives, working closely with Steven to create intuitive scheduling experiences that help people connect more efficiently and achieve their desired outcomes. His background combines deep product strategy with practical AI implementation experience.

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AI Scale Education User Experience 202