SaaStr

MARCH 1, 2025

The ideal leadership hire is someone who has seen both startups and scale. The CEO’s job is to force the leadership team to accept that their core responsibility is to phase-shift and re-architect systems regularly. Think of it as an orchestra where each section has its part, but together they create something cohesive.

Scale 191

Scale Systems Review Scaling Leadership 191

SaaStr

FEBRUARY 2, 2025

Under his leadership, the company has developed innovative AI-powered solutions for restaurant websites, online ordering, CRM, and marketing automation. Under her leadership, Alloy Automation has pioneered the use of AI to streamline API integration and documentation processes.

AI 227

AI Technical Review Artificial Intelligence Systems Review 227

SaaStr

MARCH 23, 2025

Our best hires consistently came from our leadership team’s networks. We’ve corrected this now, but we lost some early momentum.” ” Too many hiring sources initially “We spread ourselves thin across too many recruiting channels at first. We should have doubled down on this approach from day one.”

Sales Recruiting 247

Sales Recruiting Sales Hiring Scale AI 247

SaaStr

FEBRUARY 21, 2025

Here’s a deeper dive into SaaStr Annual and why it’s considered the top SaaS event: Core Elements: Takes place in the San Francisco Bay Area (usually Silicon Valley) Features over 300 speakers across multiple tracks Focuses exclusively on SaaS metrics, growth strategies, and operational excellence Typically runs for 3 days with pre and (..)

Software 246

Software Scale Venture Capital SaaS 246

SaaStr

MARCH 9, 2025

Meeting intensity KPI challenge : Sometimes AI efficiencies can reduce a company’s core metrics (like Calendly’s “meeting intensity”), requiring leadership to make conscientious decisions about value tradeoffs. That’s what Calendly’s leadership team discovered as they embarked on their AI journey.

AI 207

AI Scale Education User Experience 207

Buffer Resources

AUGUST 6, 2024

Early in my career, the idea of “thought leadership” wasn’t on my radar. My passion for narrative naturally evolved into a commitment to thought leadership, where I leverage the art of storytelling for myself and my clients to share insights, provoke discussions, and influence change.

Social Media 114

Social Media Business Leadership Sales Hiring 114

SaaStr

JANUARY 17, 2025

” This focus on quality over quick implementation has helped Zoom successfully integrate AI across 12 different products.

AI 264

AI Cybersecurity User Experience Scaling 264

SaaStr

FEBRUARY 12, 2025

Under his product leadership, Procore has grown exponentially, went public in 2021, and recently crossed the coveted $1B ARR milestone. When he joined Procore five years ago as CPO, it was a perfect fusion of his construction background and technology expertise.

Construction 255

Construction Scale SaaS Travel 255

SaaStr

MARCH 16, 2025

Prior to Datadog, Alex held leadership positions at several high-growth SaaS companies and has a proven track record of building marketing engines that deliver consistent, measurable growth. Alex Rosenblatt was the first marketing hire and Chief Marketing Officer at Datadog, all the way through IPO and beyond.

Scale 247

Scale Sales Hiring Scaling Marketing 247

SaaStr

FEBRUARY 10, 2025

Strategic Transformation The company’s leadership, including CEO Tim Sang, recognized that their challenges extended beyond typical growing pains.

Scale 165

Scale Scaling Outsourced Development Sales 165

SaaStr

SEPTEMBER 28, 2024

In reality, boards and executives are often reluctant to let go of leadership, recognizing the disruption and challenges that come with replacing key roles. But Jason reveals that these conversations often centre around confidence in your leadership rather than looking for reasons to replace you.

Technical Review 303

Technical Review Sales Hiring Sales Recruiting Revenue 303

SaaStr

FEBRUARY 5, 2025

What’s Next The next 12-18 months will be critical for SaaS companies looking to establish leadership in vertical AI. IBM’s Instruct Lab approach, delivering 98.5% cost savings and 35% time savings, shows that smaller, more focused models can often outperform larger, general-purpose ones in specific vertical applications.

AI 191

AI Scale SaaS Government 191

TechEmpower SaaS

AUGUST 21, 2023

The explanation from software leadership is often unsatisfying or unclear. Getting Buy-in from Leadership Business leaders are often concerned about how their tech teams will react to an external technical review. Let’s assume that you’ve already expressed your frustrations with technical leadership.

Technical Review 390

Technical Review Software Review Development Team Review Systems Review 390

SaaStr

MARCH 24, 2025

A new VP of Sales can add value immediately by focusing on a few critical areas that drive results and demonstrate leadership from day one: Assess and Support Top Performers : A great VP of Sales will immediately identify the top-performing reps and double down on them. Dear SaaStr: I’m Starting as a New VP of Sales.

Sales Recruiting 165

Sales Recruiting Sales Hiring Sales Leadership 165

SaaStr

JULY 23, 2024

Step 3: Realign with Leadership When coming into a new organization, you’re new. Needs a different approach to leadership. Then, align with your peer group, the executive leadership team. An essential part of getting people on board with your leadership is having empathy for the changes they’ve gone through. Support that.

Leadership 299

Leadership Scale Benchmarks Communication 299

SaaStr

NOVEMBER 23, 2022

A tenant of leadership is not just building trust, but vulnerability. Even though they’d just bought the company, everyone still had their marching orders on day one—for everything from marketing to thought leadership and enablement to assets. That vulnerability can be a building block for team trust and solid leadership.

Underperforming Technical Team 317

Underperforming Technical Team Leadership Outsourced Development Finance 317

SaaStr

DECEMBER 10, 2023

As Chief Evangelist, Udi oversees Gong’s market leadership through new product launches and thought leadership. Udi Ledergor is a five-time Marketing leader at B2B start-ups and currently the Chief Evangelist at Gong.

Leadership 349

Leadership B2B Branding Startup 349

SaaStr

JUNE 27, 2024

The Difference Between Kind and Nice Hannah asks how you balance a culture of hiring for kindness with the leadership team’s intensity for hard work, ambition, and getting things done. As you grow, you hire specialists, GTM leadership, sales leadership, and others who have done this at a similar scale or in a similar market.

Scale 264

Scale Sales Hiring Scaling Sales Recruiting 264

SaaStr

NOVEMBER 30, 2023

There’s also a management and leadership layer to enable and coach individual contributors. That’s why getting the right leadership in place is so important. But you have to have the right leadership and org structures in place in those locales, or you’re not going to see the benefit in cost savings. Net dollar retention.

Scale 278

Scale Sales Hiring Scaling Outsourced Development 278

SaaStr

DECEMBER 1, 2024

Deeper Bio: Early Life and Education Graduated with a Computer Science degree from The Academic College of Tel Aviv-Yaffo Demonstrated early interest in technology and software development Served in the Israeli Defense Forces’ Intelligence Corps, where he developed technical and leadership skills Early Career Began career as a software developer (..)

Scale 257

Scale SaaS Company Culture Leadership 257

Sales Hacker

FEBRUARY 7, 2025

The Scaling Stage: Building Market Leadership The scaling stage is where a SaaS company seeks to solidify its position as a market leader. Market leadership requires not only a compelling product but also strong brand recognition, robust customer support, and a scalable infrastructure.

Pricing 113

Pricing Scale SaaS Technical Review 113

SaaStr

DECEMBER 3, 2024

Who is Peter Gassner CEO and Founder of SaaS Leader Veeva Systems Peter Gassner has established himself as a significant figure in enterprise software, particularly through his leadership at Veeva Systems. Gassner’s leadership style is known to be product-focused and customer-centric.

SaaS 264

SaaS Leadership Cloud Enterprise 264

SaaStr

DECEMBER 17, 2023

It allows us to deliver reminders, call summaries, suggested next steps, custom prompts and easy to follow workflows directly to our market facing teams and leadership. Momentum powers a ton of automations between SalesForce, Gong and Slack for us.

Scale 298

Scale Leadership AI Innovation 298

SaaStr

AUGUST 16, 2024

years later: They build it to a $200m+ ARR business My co-founder and CTO, the most “start-up”-y guy on the team — is still there The sales team mostly stayed about 2 years after the acquisition, and then went on to sales leadership roles at Brex, Rippling, Gong, Seismic, Talkdesk, Pipedrive and so many other SaaS leaders Several (..)

Startup 316

Startup CTO Leadership Acquisition 316

SaaStr

JANUARY 10, 2024

So you need context from leadership to what you ultimately need to deliver on in your function to be successful. When you get everyone on the leadership team in a room to come up with the best ideas, those people take ownership of the ideas. Build the right leadership team based on your company’s core values and hiring principles.

Sales Hiring 311

Sales Hiring Scale Technical Review Leadership 311

SaaStr

MAY 29, 2024

It is not an innate skill, even if perhaps some of leadership is. Then I slept on it, and 2 days later said he was right, and would appreciate the opportunity. Management is a set of skills. You gotta learn. The earlier you learn, the better a shot you have at becoming a Director, a VP, and a CEO. And a better founder.

Leadership 292

Leadership Management Business 292

SaaStr

FEBRUARY 6, 2023

Promote someone great that everyone respects into a leadership role. Dear SaaStr: One of Our Most Respected Team Members Quit and Folks Are Leaving. What Do I Do? This is really the only answer I’ve seen to this situation. We’ve all been in it at least to some extent, at some level. Sometimes, a termination.

Leadership 308

Leadership Strategy Management 308

SaaStr

FEBRUARY 25, 2025

Bringing your leadership team to SaaStr Annual allows for compressed learning experiences that would otherwise take months to acquire. This holistic perspective helps you position your company more effectively and make informed strategic decisions about product direction, go-to-market approaches, and resource allocation.

Sales Recruiting 195

Sales Recruiting Scale CTO Hire Sales Hiring 195

Tom Tunguz

AUGUST 14, 2022

The company’s leadership should calculate sales efficiency on the combined OTE (on-target earnings) to quota ratio of these teams. Sometimes, these plans have a minimum contract value plus a bounty. Another structure establishes land account executives & expand account executives. A land AE with a $300k OTE might have a $600k quota.

Startup 342

Startup Construction Sales Compensation 342

SaaStr

APRIL 1, 2023

We hired job hoppers that never stayed anywhere for more than 18 months for leadership roles. This data from Carta helps illustrate it: So we cut corners. We stopped doing reference checks. No time, didn’t want to know. We all did, just to get it done. And now we’re paying the price.

Sales Hiring 316

Sales Hiring Investment Leadership Startup 316