How CFOs and CTOs buy B2B software in 2025

A data-first look at how CFOs and CTOs buy in 2025. Where they look, how they judge ROI and risk, and what they choose to buy.
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Market research

How CFOs and CTOs buy B2B software in 2025

A data-first look at how CFOs and CTOs buy in 2025. Where they look, how they judge ROI and risk, and what they choose to buy.

01.
Introduction

Behind every major B2B software purchase stands two critical signatures: the financial leader who controls the budget and the technology leader who sets and enforces standards.

A perfectly tailored pitch means nothing without both approvals. The CFO scrutinizes ROI while the CTO evaluates integration. One focuses on financial risk, the other on technical debt. Miss either perspective, and your deal won't happen.

We used Wynter to survey 200 B2B SaaS leaders - 100 CFOs and VPs of Finance, and 100 CTOs, CIOs, and VPs of Technology at companies with $50M+ revenue. We uncovered how they evaluate vendors, where they look for information, and what ultimately makes them say "yes."

These insights reveal precisely what both audiences care about, what raises red flags, and how to earn approval from both sides of the decision table.

02.
CFO vs CTO: two parallel buying tracks

While marketing often treats "the buying committee" as a single entity, financial and technology leaders have different triggers for involvement, distinct research methods, and separate criteria for success. Understanding their requirements is the difference between deals that stall and deals that close.

How financial leaders engage

Only 16% lead end-to-end vendor selection. The rest appear exactly when (and only when) they need to.

Their involvement varies based on company size, purchase amount, and potential risk:

Final approval (30%): These financial leaders position themselves as ultimate gatekeepers, reviewing what their teams bring them and making the final call.

The CFO stamp comes at the end of the process, to ensure that the expense is included in the budget. So this is a yes/no/challenge role.
— Geoffrey, CFO, 501-1000 Employees, Manufacturing

Consult approach (20%): They serve as trusted advisors, offering strategic guidance while teams drive the research.

I'll help define the success criteria of the software we're looking for and narrow down the list of candidates.
— Adrian, VP of Finance, 201-500 Employees, SaaS/Software

End-to-end oversight (16%): Most common in smaller companies (201-500 employees), these leaders stay hands-on from day one to signature.

I am involved in all aspects of the buying process. I demo the services for functionality and gauge value and pricing.
— Steven, CFO, 201-500 Employees, Staffing and Recruiting

Negotiations-based (12%): They swoop in specifically for deal-making when pricing or contract terms need work.

My role is to support with price and contractual terms.
— Daniel, CFO, 201-500 Employees, Staffing and Recruiting

How technology leaders engage

Every tech investment begins with a pain point. Tech leaders start by defining problems with precision before entering vendor research:

We will start with a long list and get to a short list of 2-3. That shortlist will ultimately get to a side-by-side comparison of functionality, technical fit, vendor strength/stability, cost, and support/services.
— Tom, Chief Information Officer, 1001-5000 Employees, Healthcare

Their research approaches break down into four distinct styles:

Delegators (25%): Trust specialized teams to conduct research, stepping in for final validation.

I do very little review myself. I trust the subject matter experts to research and apply how the candidate tools might best solve our problem.
— Steve, Chief Information Officer, 5001-10000 Employees, Education

Hybrid approach (22%): Conduct initial research before delegating to teams.

I lead the initial research... once I narrow it down to 5-10 vendors, I delegate: IT team → Security check, end-users → usability feedback, finance → ROI analysis.
— Aidan, Chief Information Officer, 201-500 Employees, Healthcare

Solo researchers (13%): Manage the entire research process personally.

I normally do all of my own research for tooling to ensure I have all the proper context.
— Justin, Chief Information Officer, 501-1001 Employees, Technical Services

50/50 split (12%): Share responsibility with teams, focusing on different aspects.

The team deals in functionality, I deal in financials, support, reputation, references.
— Michael, SVP CIO, 1001-5000 Employees, Healthcare

The price tag trigger

While involvement styles vary, one factor consistently determines financial leaders' attention level: the price tag.

For all processes within finance, I will jump in evaluations over $1 million contract value.
— Teddy, VP of Finance, 501-1000 Employees, IT Services and IT Consulting
I am involved in all purchases over $2500.
— Kevin, CFO, 1001-5000 Employees, SaaS/Software

Once you cross their financial threshold, they're asking:

  • Does this align with our financial strategy?
  • What ROI metrics justify this expense?
  • Are the contract terms favorable?
  • Is this vendor financially stable?

Key insight: The hidden orchestration challenge

Here's what most vendors miss: financial and technology leaders rarely coordinate their evaluation processes. Tech leaders are testing your product while CFOs are questioning your financials. One focuses on "Can it work?" while the other asks "Should we pay for it?"

Our advice: You need to satisfy both audiences simultaneously, even though they're evaluating you through completely different lenses at different times. By recognizing this dual-track reality and designing your sales process to address both perspectives proactively, you'll avoid having to scramble to satisfy each stakeholder as they appear.

Your action plan: Map out when each leader type typically engages based on deal size and company profile. Create stage-appropriate materials that speak to their specific concerns. Most importantly, help them help each other. Give tech leaders the financial ammunition they need to satisfy CFO concerns, and provide financial leaders with enough technical clarity to trust the CTO's recommendation.

03.
Where buyers actually discover vendors in 2025

The death of traditional marketing? Not quite. But the way B2B leaders discover software has fundamentally shifted from vendor-controlled channels to peer-driven networks.

While financial leaders start with trusted peers, technology leaders begin with Google. This split reveals why many marketing strategies fail. They assume a single discovery path when buyers actually take two completely different journeys to find you.

CFOs path: dark social → Google → review sites

Financial leaders follow what we call the "three-stage screening process":

Stage 1: Dark social (72%) The majority turn to peers before any formal research begins.

I'll go on LinkedIn and CFO groups I'm a member of, usually people in the same industry have some kind of best in class vendors they already have experience with.
— Matan, VP of Finance, 201-500 Employees, IT Services and IT Consulting

Stage 2: Google (64%) They use search to compile lists and validate recommendations.

I go to google and search for reviews.
— Ross, Chief Financial Officer, 501-1000 Employees, SaaS/Software

Stage 3: Review sites (30%) Gartner and similar platforms serve as verification layers.

We review comparison websites like G2, Gartner Magic Quadrant, and similar services.
— Matt, CFO, 1001-5000 Employees, SaaS/Software

CTOs path: Google → peers → analyst reports

Tech leaders take a more hands-on approach to discovery:

Google leads (73%) Nearly three-quarters begin with direct searches.

Google is usually the first place to search for solutions and compare vendors.
— Ian, Chief Technology Officer, 1001-5000 Employees, SaaS/Software

Peer validation (53%) Over half consult their networks, but often after initial research.

I might Google, but wouldn't trust those results. I would definitely speak to my peers.
— Tom, Chief Information Officer, 1001-5000 Employees, Healthcare

Industry insights (23%) Almost one in four check analyst reports.

We explore trusted industry sources such as Gartner, Forrester, and IDC reports for vendor comparisons.
— Vishnu, Chief Financial Technology Officer, 201-500 Employees, Financial Services

AI in vendor discovery (who uses what)

Both audiences are adopting AI tools, though at different rates:

  • 12% of financial leaders use AI for vendor discovery
  • 20% of tech leaders incorporate AI into their research
LLMs (ChatGPT, Perplexity, Mistral) to get an exhaustive list of comparable solutions... I look into the solutions' website to understand if they meet the technical requirements.
— Geoffrey, CFO, 501-1000 Employees, Manufacturing
Always ChatGPT now! It used to be product hunt or Reddit.
— Aaron, Chief Information Officer, 201-500 Employees, Telecommunications‍

Why vendors stay invisible to one side

The most striking finding? Financial leaders discover vendors through relationships while tech leaders discover through research. This creates a fundamental challenge: optimizing for one audience may make you invisible to the other.

Consider this scenario: A CFO hears about you from a peer at a conference. Meanwhile, their CTO is Googling solutions and building a completely different shortlist. If you're not present in both discovery channels, you've already lost half the battle.

The winners are vendors who own this dual-channel reality. They'll build strong peer advocacy programs to capture financial leaders while maintaining great SEO, adapting for AEO, and producing helpful content to catch technology leaders. Most importantly, they'll recognize that being discovered is no longer about choosing the right channel, it's about being present across all the channels your buyers actually use.

Your action plan: Audit your current discovery strategy. Are you equally visible to both peer networks and search engines? If not, you're leaving deals on the table.

04.
Building the shortlist

Making the shortlist isn't necessarily about being the best solution available. It's about being the most trusted solution at the exact moment your buyers are looking.

Our data reveals a harsh truth: by the time vendors know they're being evaluated, the shortlist is often already set. Financial leaders verify what their teams recommend. Technology leaders narrow down from 5-7 options to 2-3 finalists. Both approach this phase with serious skepticism and a rigorous criteria.

Finance: trust but verify

56% of financial leaders take a "trust but verify" approach to vendor research:

Typically I start with what the team provides me and then I do research on my own to verify.
— Doug, CFO, 201-500 Employees, SaaS/Software

22% adjust involvement based on purchase type:

If it is related to finance or legal, I like to do my own research. In other areas, I trust what the respective team has researched.
— Joel, CFO, 1001-5000 Employees, SaaS/Software

Tech: how process shifts by company size

Decision-making processes vary significantly by organization scale:

Enterprise (10,000+ employees)

  • Multiple stakeholders beyond core decision-makers
  • Rigorous security evaluation and compliance reviews
  • 30% use formal RFP processes

Mid-sized (500-5000 employees)

  • Faster sales cycles with structured flexibility
  • Hands-on evaluation through trials and sandboxes
  • Balance between thorough evaluation and speed

Smaller companies (201-500 employees)

  • Direct decision-making with minimal approval layers
  • 27% prefer pure self-service purchasing
  • Speed of implementation crucial
I always try to get a free trial to play around with the actual software instead of taking a PowerPoint's word for it.
— Louis, SVP Technology, 201-500 Employees, SaaS/Software

Shortlist mismatch: get on both lists

Financial and technology leaders often build different shortlists for the same purchase. The CFO's list comes from trusted peer recommendations. The CTO's list emerges from technical research and hands-on testing. When these lists don't overlap, buying comittee dynamics can derail or delay purchases.

Your competitive advantage: Instead of hoping stakeholders will advocate for you across departments, proactively bridge the gap. Create materials that help tech leaders speak the CFO's language and give financial leaders enough technical confidence to support the CTO's choice.

Remember: The goal is to be the only vendor that appears on everyone's list.

05.
How buyers evaluate before talking to sales

The reality is, you’re not steering the buyer’s journey anymore. By the time your sales team hears from them, many have already made up their minds.

In our research, 84% of tech leaders review vendors before any sales call. And 78% of finance leaders verify their teams’ picks on their own. That means your solution is judged from multiple angles, often at the same time and when you’re not in the room.

What CFOs scrutinize: TCO, custom ROI models, references

Total cost of ownership (66%) They look beyond year one to 3-5 year commitments.

"I analyze the annualized cost (depreciation of implementation + recurring subscription + indirect costs) in comparison to savings expected to be realized." - Brenda, CFO, 201-500 Employees, Financial Services

Custom frameworks (56%) Over half create their own evaluation models, as 58% don't trust vendor ROI calculations.

I do not really trust their calculations as it is very skewed.
— Tammy, CFO, 201-500 Employees, IT Services and IT Consulting

Reference checks (36%) They verify case studies and speak with current customers.

Case studies are helpful and customer referrals are more helpful.
— Bryn, CFO, 201-500 Employees, SaaS/Software

What CTOs examine: Website clarity, trials, security, reviews

Website clarity (100%) Every tech leader visits vendor websites, expecting immediate answers.

Before our sales call, I'll have reviewed their website, case studies, and available reviews or testimonials.
— Shad, Chief Technology Officer, 1001-5000 Employees, Education

Interactive demos (83%) They need hands-on experience before sales conversations.

We will always try to get a free trial to play around with the actual software instead of taking a PowerPoint's word for it.
— Louis, SVP Technology, 201-500 Employees, B2B SaaS

Peer reviews (70%) They deep-dive on review sites for unfiltered truth.

I would also look to G2 Crowd and Capterra to see what others are saying.
— Davi, Chief Information Officer, 201-500 Employees, Non-Profit

The evaluation reality check: You're being judged before you know it

The takeaway from our research: your website does most of the selling for tech leaders. They'll be testing your product, checking your security docs, and comparing you to competitors all before reaching out. Financial leaders are building their own ROI models, calling your customers, and verifying every claim you make.

This invisible evaluation phase determines whether you'll get a chance to demo. By the time you're invited to present, buyers have already decided if you're a contender or just checking a box.

In short, your self-service evaluation experience must be as good as your best sales demo. Every touchpoint should anticipate and answer the questions both audiences are asking. Most vendors still optimize for the sales call that may never come, while winners optimize for the evaluation that's already happening.

Our advice: Audit your digital presence through both lenses. Can a CFO find ROI data without a demo request? Can a CTO test core functionality without talking to sales? If not, you’re losing deals at the starting line.

06.
Decision criteria that make or break deals

Every vendor claims superior ROI and seamless integration. So why do some win while others lose? The answer lies in understanding the hidden hierarchy of decision criteria.

Financial leader priorities

When deciding whether to approve, financial leaders prioritize these factors:

  1. Cost (76%) - Budget fit and total investment
  2. ROI (48%) - Both hard and soft returns
  3. Business need (34%) - Must solve real problems
  4. Risk (20%) - Vendor stability and implementation challenges
  5. Implementation (14%) - Team adoption likelihood
Pricing is by far our most important criteria.
— Maydan, CFO, 201-500 Employees, SaaS/Software
ROI is always number one, do I actually believe the ROI will come?
— Matan, VP of Finance, 201-500 Employees, IT Services and IT Consulting
"ROI is always number one, do I actually believe the ROI will come?" - Matan, VP of Finance, 201-500 Employees, IT Services & IT Consulting

Technology leader priorities

Tech leaders focus on different aspects:

  1. Problem-solving capability - 39% of CTOs explicitly said they would choose a startup over enterprise if their solution is a better fit
  2. Technical fit - Integration with existing stack
  3. Security and compliance - Especially for mission-critical systems
  4. Support quality - Vendor responsiveness and expertise
The goal of spending money on a new vendor is generally to solve a problem. The only reason to use a vendor solely for their brand is if the relationship could drive additional revenue.
— Louis, SVP Technology, 201-500 Employees, B2B SaaS/Software

The criteria conflict: When priorities collide

Here's where deals get complicated: the CFO's top priority (cost) often conflicts with the CTO's top priority (problem-solving capability). The best technical solution might not offer the best ROI. The most cost-effective option might create integration nightmares.

This tension explains why so many deals stall in the final stages. Without alignment, nobody wins.

Your action plan: Stop selling to job titles and start solving for criteria conflicts. Build business cases that explicitly address both value systems. Better yet, help your champions do it for you by providing materials that translate technical value into financial terms and financial benefits into technical advantages.

07.
The business case that wins both signatures

The main goal here is about helping both leaders justify the decision to each other. Here's exactly what they told us they need:

Financial leaders require

Detailed cost & ROI analysis

  • Granular breakdowns
  • Multi-year projections
  • The data to make their own ROI calculations

Feature comparisons

  • Side-by-side analysis
  • Productivity gains in real numbers

Risk assessment

  • Vendor stability evaluation
  • Security concerns
  • Exit strategy options

Technology leaders require

Clear differentiation

  • Why your solution over competitors
  • Specific technical advantages
  • Integration capabilities

Hands-on validation

  • Free trials or sandbox environments
  • Real-world testing scenarios
  • No artificial barriers

Peer validation

  • References from similar companies
  • Unfiltered customer feedback
  • Industry-specific use cases

08.
How B2B leaders prefer to buy

The future of B2B sales is already happening right now, it's just unevenly distributed. While vendors invest in traditional sales motions, buyers are quietly revolutionizing how they want to purchase.

Our data reveals a striking contradiction: 57% of tech leaders prefer traditional sales demos, yet 83% want to self-serve before any sales conversation. This is a fundamental shift in how B2B buyers want to engage with vendors. They want both self-service and human expertise, just at different moments in their journey.

The demo paradox

57% of tech leaders prefer traditional sales demos, with 86% currently purchasing this way. Yet 83% also want self-service exploration before any sales conversation.

We request a demo to get deeper insights on usability, vendor compliance with our policies, important features, ROI and what differentiates them on the market.
— Ryan, Senior Vice President Chief Information Officer, 10,000 Employees, Manufacturing

Financial leaders view demos differently, as opportunities to verify claims and assess vendor credibility rather than explore functionality.

The self-service trend

  • 24% of tech leaders prefer pure self-service
  • 27% of smaller companies want minimal sales interaction
  • Both audiences expect frictionless trials

The hybrid future: Self-serve discovery, human expertise for decisions

The most successful vendors in 2025 won't force buyers to choose between self-service and sales support. They'll offer both, designed for where buyers are in their journey and what they're trying to achieve.

Tech leaders want to explore independently first, testing integrations and validating functionality without sales pressure. But when it's time to navigate organizational dynamics or negotiate terms, they value expert guidance. Financial leaders want to verify ROI claims independently but appreciate strategic discussions about long-term value and risk mitigation.

This hybrid model requires rethinking traditional sales stages. Instead of controlling information flow to force sales conversations, companies doing this best provide full transparency while positioning their sales teams as advisors for complex decisions. They recognize that buyers will self-educate regardless.

Our advice: Map out which parts of your sales process truly require human interaction and which create unnecessary friction. Enable technical self-service while positioning sales conversations around strategic value, risk mitigation, and organizational change management. The goal is to use your sales team where they add genuine value rather than serve as information gatekeepers.

09.
Winning strategies for both audiences

Success in B2B sales once meant mastering a single playbook. In 2025, it requires conducting two different plays at once.

The vendors who thrive will be those who stop trying to force-fit one approach for all stakeholders and instead build dual excellence.

For financial leaders

  1. Provide transparent data for their custom calculations
  2. Address risk upfront with mitigation strategies
  3. Show clear ROI with conservative projections
  4. Prepare for verification - they will check everything

For technology leaders

  1. Make your website your best salesperson with clear differentiation
  2. Offer frictionless trials and interactive demos
  3. Build peer advocacy - their networks matter most
  4. Focus on solving specific problems better than anyone else

Universal truths

Both audiences share common requirements:

  • Peer validation carries more weight than vendor claims
  • They research extensively before any sales conversation
  • Trust must be earned through transparency and proof
  • ROI and risk assessment drive final decisions

CFOs don't dislike spending, we dislike wasting money. Speak in financial outcomes, not just marketing metrics.
— Yulia, CFO, 501-1000 Employees, Marketing and Advertising

The orchestration challenge: Making two audiences come together

The biggest revelation from our research is that your role isn't just to satisfy both audiences separately but to help them build consensus together.

This requires a fundamental shift in sales strategy. Instead of sequential selling (convince the CTO, then the CFO), enablement needs to be simultaneous. Companies need to provide materials that help technical leaders make financial arguments and financial leaders understand technical value. They recognize that internal champions need ammunition for conversations that happen without vendor presence.

The path forward isn't about choosing which audience to prioritize, it's about recognizing you need both signatures to win.

Here's our advice on how to get CFO and CTO buy-in in 2025:

  • Build discovery strategies that work for both peer networks and search engines
  • Create evaluation experiences that satisfy both technical testing and financial analysis
  • Develop business cases that translate between technical and financial value systems
  • Enable champions to advocate across functional boundaries
  • Recognize that trust, built through transparency and customer advocacy, is more effective than traditional sales tactics

Meet them where they are with transparency, genuine value, and respect for their needs. Skip the hype, deliver the substance, and recognize that your best advocates are your current customers telling their peers you're worth the investment.

Get the full report here

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