🔥 Five SaaS acquisitions just dropped

ISSUE #260

The M&A winter might be thawing. Back in October, Tomasz Tunguz painted a grim picture of tech acquisitions, noting 2023-24 hit 12-year lows. But 2025? It's telling a different story 👀.

Just three weeks in, and we've already seen five major cloud companies whip out their checkbooks. From Datadog to ServiceNow, it seems the "build vs. buy" pendulum is swinging back to shopping season 🛍️.

In this week's roundup, we cover:

• The SaaS shopping spree: Cloud M&A is heating up (again)

• The evolution of sales leadership: Your stage-by-stage guide from $0 to $50M

• Custom GPTs in sales: How AI is becoming every rep's secret weapon

Let's dive in!

Ian at SaaS Weekly

INDUSTRY ROUNDUP

🤝 Acquisitions | The SaaS shopping spree shows no signs of slowing
Five deals dropped and we’re only three weeks into the year! Cloud companies are keeping their M&A engines running hot, following an uptick in activity at the close of 2024:

• Datadog acquires Quickwit

• ServiceNow acquires Cuein

• Trade Desk acquires Sincerta

• Clearwater Analytics acquires Enfusion

• AvePoint acquires Ydentic

🥁 Jobs | And the hottest job title of 2025 is...
LinkedIn's latest Jobs on the Rise report crowns "AI Engineer" and "AI Consultant" as the winners – looks like adding "AI" to your profile is the new Growth Hacker role. (Link)

🎯 Marketing | 3 CTA tweaks that are crushing conversions
Swapping "Buy Now" buttons for low-friction, product-first CTAs is making cash registers ring – and it’s making your stale "Sign Up" button jealous. (Link)

📱 Social | The secret sauce to LinkedIn virality isn't what you think
From universal topics that spark comment frenzies to spicy hot-takes that start debates, a deep dive reveals LinkedIn's algorithm loves drama (🤷🏻‍♂️) – but only if you can keep it authentic. (Link)

FOR YOUR COMMUTE

🎙How Practical Founders Are Winning Big with Growth Equity Funding
Practical Founders

🎙HubSpot: An Underdog Takes on Goliath
Crucible Moments | Sequoia Podcast

FROM THE TRENCHES

LEADERS ON LINKEDIN

GROWTH PLAYS IN PRACTICE

🏓 Framework | 3 min read | Sophie Buonassisi, The GTM Newsletter
The 5-phase framework that grew Outreach from $0 to $230M ARR

In theory: As startups scale, the role of sales leadership evolves through distinct phases, each requiring different skills and focus areas.

While frameworks like MEDDIC and Sandler focus on sales execution, Outreach's 5-phase leadership framework (Doer, Builder, Doctor, Architect, Communicator) shows how sales leadership must transform to match company growth stages.

In practice:

1. Start with a revenue-focused Doer ($0-1M ARR): Hire your first salesperson on commission-only with a proven network and ability to build their own team. Outreach's first hire hit $1M in 6 months by focusing purely on selling, not strategy.

2. Transition to a Builder ($1-10M ARR): Only add new reps when existing reps hit 25 active opportunities. Build initial processes through trusted network hires who can establish culture and stay long-term.

3. Let the Doctor diagnose ($10-25M ARR): Instead of waiting for pipeline, hire ahead for capacity then drive demand to fill it. This reverses early-stage hiring where pipeline comes first.

4. Scale through the Architect ($25-50M ARR): Design scalable blueprints for each market segment while maintaining cultural cohesion. Focus on hiring second-line leaders who can create their version of your culture.

🏓 Strategy | 5 min read | April Dunford, Positioning with April Dunford
How to turn a competitor's strength into a weakness

In theory: Traditional SWOT analysis takes a broad, static view of competitive dynamics - listing out strengths, weaknesses, opportunities, and threats as fixed attributes.

In contrast, April Dunford's "positioning jujutsu" framework offers a more tactical approach: deliberately reframing competitor strengths as weaknesses for specific customer segments.

In practice:

1. Win against market leaders by specializing: Instead of competing broadly, target segments where the leader's "one-size-fits-all" approach fails. Hubspot did this by focusing on SMB marketing automation while Eloqua and Marketo fought over enterprises.

2. Position against platforms through speed: When competing with all-in-one platforms, emphasize faster deployment and adoption of your point solution. Focus on the 1-2 critical workflows where you excel, rather than trying to match the platform's breadth.

3. Beat free products by targeting different buyers: Don't sell to end-users where free products win. Instead, target managers and executives who need enterprise features like cross-team analytics and governance. They'll pay for capabilities that free products can't match.

TOP READS FROM LAST WEEK

1. The Rise of Free SaaS Tools as Lead Magnets (Link)

2. From AI agents to enterprise budgets, 20 VCs share their predictions on enterprise tech in 2025 (Link)

3. The Unfair Advantages Framework (Link)