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” I saw a term sheet the other day where a leading VC firm reserved $1m of the round … for hiring a “VP of AI” Leadership teams scrambling to post job descriptions for “Head of Artificial Intelligence.” Board meetings where someone inevitably asks, “Don’t we need a VP of AI?”
The Current State of Leadership Tenures in SaaS Brian sets the stage frankly on how hiring has gone at HubSpot: “We’ve hired a lot of executives, but many haven’t worked out.” Our head of product, head of engineering, like pretty much everybody in leadership. They grew up in their career with us.
Technical Decision Makers : These are your “10x engineers” – the architects and principal engineers who may not have leadership titles but carry massive influence with leadership. CTO/Engineering Leadership : The final approvers who need to see clear business value and ROI.
When to Hire Executives But there are three other factors that I tell companies to consider when hiring finance leaders (or any other department leaders): Leaders cost Capabilities of current leadership Complexities and needs of the business These factors will help you determine when you need a true CFO. Source: Pave 2. Can they fill gaps?
Whether you're making the case to leadership or validating outsourcing, this toolkit gives you the numbers and tools you need. This guide helps you quantify hidden costs like developer time, support overhead, tech debt, and lost revenue.
” What Will AI Change in Go-to-Market “It will lead to a next level of transparency for leadership,” Jason answers. So we should learn from it in sales for leadership, for transparency, for product, because here’s your crystal ball. It will be a big change and a lot of friction.
Account Research : Instead of reps spending hours researching prospects, AI can instantly analyze company financials, recent news, leadership changes, technology stack, and competitive positioningthen synthesize it into actionable insights. AI eliminates entire categories of work.
Databricks’ VP of Sales on “Proven Leadership Frameworks For a High Performing Sales Team” The post 5 Great SaaStr Sessions with Databricks’ CEO, CMO, GM, VPP and VPS! The 7 Biggest Mistakes CMOs Make with Databricks’ CMO Rick Shultz #4. The Top 5 Lessons Learned Scaling Databricks’ to $1.5B
The learning: When you solve a genuinely hard problem, you get three moats for free: Technical advantage through innovation Legal protection through patents Thought leadership in the space 2. Solve Hard Technical Problems Create multiple moats Patent protection Technical innovation Market leadership 2.
It will help you understand: Where you stand in the five stages of payment integration, why you want to get to the next level, and how to do it How to create new revenue streams with premium payment services such as detailed transaction analytics, tokenization, and advanced fraud prevention tools How to ensure your payments strategy not only supports (..)
This requires entirely new management skills focused on systems optimization, not just people leadership. The CRO Hiring Playbook Has Forever Changed The interview process for revenue leadership roles now at Owner includes a mandatory AI component. You need weekly refinement cycles and deep involvement from revenue leadership.”
Strong Market Education Both invest heavily in educating their markets: HubSpot created the inbound marketing movement through blogs, certifications, and events Monday.com uses its platform to showcase innovative work management approaches This education creates category leadership and drives organic adoption.
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.
Bottom Line : These 10 metrics show how world-class SaaS companies evolve from growth engines to profit machines while maintaining market leadership. The slight Q1 dip (42% vs 43%) shows even great companies face quarterly fluctuations – focus on the trend, not single data points.
Speaker: Peter Cowen, Managing Director, Sutton Capital Partners & Tim Draper, Founder, Draper Associates
What are some examples of companies and leadership that has impressed you? What sectors (e.g. ecommerce) are gaining traction in this new world? Can you provide business metrics you are prioritizing now more than you were a few months ago? What is something surprising/inspiring that you learned during COVID-19?
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.
If key stakeholders or end-users see the value during the pilot, its much easier for the client to justify the investment to their leadership team. Internal Buy-In : For enterprise clients, a pilot can help them build internal support for your product. Hands-On Experience : Pilots provide clients with a hands-on experience of your product.
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 (..)
Evolve your leadership : Great leaders consistently manage themselves out of the job. One-on-Ones and Feedback Structure your 1:1s : Use a four-part format covering performance, relationships, leadership, and innovation. Design intentionally : Make sure you’re designing your organization with a span of control in mind.
Speaker: Richard Cardran, Chief Creative Officer and VP Strategy, HIA Technologies
Innovation and Leadership go hand in hand. We'll examine the importance of UX and user-centric feature analysis, the adaptation of Agile Methodologies to the creative process, as well as a way to drive successful culture change for setting expectations and winning approvals with cross-functional stakeholders.
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.
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.”
Category Leadership Indicators What It Is : Market share growth, pricing power, competitive win rates The Benchmark : Top 3 in category with defendable differentiation Why It Matters : Public investors pay for market leaders. Reddit’s platform network effects created clear category leadership.
OpenAI maintains overall market leadership, but the breakdown is telling: 67% of OpenAI users deploy non-frontier models vs. only 41% for Google and 27% for Anthropic. Multi-Model Deployment Is Crushing Single-Vendor Strategies The Hard Data : 37% of enterprises now use 5+ models in production (up from 29% last year). Flash costs $0.26/million
What are some examples of companies and leadership that has impressed you? What sectors (e.g. ecommerce) are gaining traction in this new world? Can you provide business metrics you are prioritizing now more than you were a few months ago? What is something surprising/inspiring that you learned during COVID-19?
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.
Even more telling: OpenAI, despite maintaining market leadership at 33.9%, has actually seemingly lost some ground from its peak share levels. While overall AI penetration among U.S. businesses has reached an incredible 41.7% as of April 2025, the growth trajectory has flattened since late 2024.
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.
Speaker: Peter Cowen, Managing Director, Sutton Capital Partners & Ben Narasin, Venture Partner, NEA
What are some examples of companies and leadership that has impressed you? What sectors (e.g. ecommerce) are gaining traction in this new world? Can you provide business metrics you are prioritizing now more than you were a few months ago? What is something surprising/inspiring that you learned during COVID-19?
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.
Leadership Style As CEO, Couremanche was known for fostering a strong company culture. Company Growth and IPO Under his leadership, Procore grew from a small startup to a major player in construction technology. The company started in a small office above a Santa Barbara surf shop.
If your engineering team, your product team, or your leadership team hasn’t shipped meaningful AI capabilities into production by now, that have led to a material increase in revenue — you don’t have a strategy problem. That requires leadership that understands both the technology possibilities and the market implications.
What are some examples of companies and leadership that has impressed you? What sectors (e.g. ecommerce) are gaining traction in this new world? Can you provide business metrics you are prioritizing now more than you were a few months ago? What is something surprising/inspiring that you learned during COVID-19?
Companies that develop organizational designs and executive practices optimized for AI orchestration will outperform those treating AI as merely “faster humans.” ” Where Do We Go From Here?
Its founders and many of the current leadership team all started as developers. Since its original inception in 2021, Copilot has evolved and grown to 77,000 organizations and almost 2 million users. GitHub focuses on creating developer-centric tools, drawing from GitHub’s long-standing commitment to the developer community.
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.
Speaker: John Mansour - President, Product Management University
You’ve come up with a winning product strategy, everyone’s on board and energized, and you’re halfway down the path to execution only to have it submarined by something someone convinced your leadership was more strategic!
This kind of leadership is contagious. By getting out there and closing deals yourself, you set the tone for your team. You show them that youre committed, that you believe in the product, and that youre willing to do the hard work. If customers arent buying, youll know immediatelyand youll have to figure out why.
The ultimate gathering of SaaS and AI leadership is about to happen in San Francisco. It’s days away now! SaaStr Annual + SaaStr AI Summit 2025! We’re bringing together the true founders, revenue leaders and product visionaries that are actually driving the next wave of AI first software. Not talking heads. Not theorists.
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.
Budget Cuts or Organizational Changes : If you hear about budget tightening, restructuring, or new leadership, its a warning sign. When a CMO leaves at a sponsor, there’s more than a 50% chance they don’t renew. These shifts can lead to reevaluations of tools and vendors, even if engagement is high.
This is just one of the findings in this year’s State of Product Leadership report. Delivery is the top success metric for product leaders. But should it be? Download the report to discover more ways product management is changing in 2021.
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