Discovery Call Prep Brief: Calendly

Company Quick Facts

• Industry: B2B SaaS - Scheduling & Productivity Software
• Size: ~600-650 employees (remote-first)
• Stage: Series B funded ($350.6M total raised, Jan 2021)
• Valuation: $3B (2021 Series B)
• Revenue: $276.1M (2023), up from $181.5M (2022)
• Headquarters: Atlanta, GA (fully remote since July 2021)
• Founded: 2013 by Tope Awotona
• Customer Base: 20+ million users across 230+ countries

Recent Developments (Last 90 Days)

Major Partnership: LinkedIn Integration (March 20, 2025)

• Calendly integrated with LinkedIn to allow Premium Business subscribers to add “Book an Appointment” buttons directly to their profiles
• Enables direct meeting scheduling without external links
• 165,000+ LinkedIn users already feature Calendly links
• LinkedIn Premium subscribers using custom buttons see 25% more profile views on average
• Strategic move to deepen enterprise market penetration through professional networks

Product Updates (Q4 2024 - Q1 2025)

• Revamped Integrations & Apps page with improved discovery and management capabilities
• Added multiple location options to One-on-One and Collective Event Types for greater flexibility
• New Gong browser integration for seamless email workflow
• Continued enhancement of recruitment scheduling capabilities following Prelude acquisition (2022)

Strategic Context

• Enterprise Focus: Moving deeper into enterprise market, already serving Fortune 500 companies
• Remote-First Organization: Fully distributed workforce across 6 continents since 2021
• Profitability: Company is profitable (unusual for SaaS at this scale)
• Active Hiring: More open engineering and technical roles than any time in past 6 months (SQL, Go, Ruby, Python, Java, PostgreSQL, Google Cloud)
• Strategic Acquisitions: First acquisition (Prelude, 2022) signals growth-by-acquisition strategy

CFO Persona: David Chen

Note: Limited public information available on David Chen as CFO of Calendly. The following analysis is based on role-specific challenges for a CFO at a company of Calendly’s profile.

Pain Points for CFO at Growth-Stage SaaS Company

1. Scaling Financial Operations Without Scaling Headcount

• 20M users, $276M revenue, 650 employees = high revenue per employee (~$425K)
• Remote-first across 6 continents = distributed expense management complexity
• Need to maintain efficiency ratios while growing 50%+ YoY
• Manual expense processes break at scale, especially across time zones and currencies

2. Distributed Workforce Expense Visibility

• 650 employees working remotely across 230+ countries
• Multiple currencies, tax jurisdictions, and compliance requirements
• Travel & Entertainment expenses difficult to track in real-time
• Shadow spend from distributed purchasing (team leads buying tools independently)
• Average SaaS company: 51% of software transactions not tagged as “software” in expense systems

3. SaaS Spend Explosion

• SaaS companies spending $4,000 per employee on average = ~$2.6M annual software spend
• Shadow IT accounts for 40% of applications in typical organizations
• Business units now control 70% of SaaS spend (vs. centralized IT)
• With active hiring across engineering/sales/CS, tool proliferation accelerating
• Duplicate subscriptions across departments (Zoom, Slack, analytics tools, etc.)

4. Board & Investor Reporting Pressure

• Series B investors (OpenView, ICONIQ) expect sophisticated unit economics reporting
• Need to demonstrate efficient growth (Rule of 40, EGS - Growth relative to burn)
• Tracking NDR (Net Dollar Retention), CAC payback, LTV:CAC ratios
• Real-time visibility into ARR, churn, expansion revenue
• Pressure to maintain profitability while investing in growth

5. Enterprise Pivot = Complex Expense Patterns

• Moving upmarket to larger enterprise customers
• Increased travel for enterprise sales, customer success, executive relationships
• More expensive conferences, sponsorships, and industry events
• Strategic partnerships (like LinkedIn) require co-marketing spend
• Sales team travel budgets growing with enterprise focus

6. Compliance Across Jurisdictions

• Employees in 6+ continents = VAT, GST, sales tax compliance complexity
• SOC 2, GDPR, data privacy requirements for enterprise customers
• Tax implications of remote workforce (nexus issues)
• Expense policy enforcement across cultures and regions
• Audit trail requirements for distributed expense approvals

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Discovery Questions (Organized by Topic)

Opening / Rapport Building (5 min)

1. “Congrats on the LinkedIn partnership announcement in March! That’s a strategic move. How has reception been from your enterprise customer base?”

   • Why: Build rapport, show you did homework, understand enterprise strategy

2. “I saw Calendly’s at $276M in revenue and profitable - rare in SaaS. What’s your north star metric you’re optimizing for right now?”

   • Why: Understand CFO priorities beyond growth-at-all-costs

Current State: Expense Management (8 min)

3. “With 650 employees distributed across 6 continents, walk me through how expense management works today. What systems are you using?”

   • Why: Baseline current state, identify legacy tools

4. “How long does month-end close typically take with a fully remote, globally distributed team?”

   • Why: Quantify inefficiency, establish baseline metric

5. “What percentage of expenses come in after-the-fact via receipt submissions vs. being pre-approved or controlled upfront?”

   • Why: Identify reactive vs. proactive spend control

6. “You’re hiring aggressively in engineering and sales. How are you maintaining visibility into spending as headcount grows?”

   • Why: Tie growth to pain point, force them to articulate challenge

SaaS & Software Spend (7 min)

7. “At your scale, you’re probably spending $2-3M annually on SaaS tools. Do you have visibility into every subscription across all departments?”

   • Why: Surface shadow IT problem

8. “When a team lead wants to purchase a new tool - Figma, Notion, another analytics platform - what’s the approval process? How do you prevent duplicate subscriptions?”

   • Why: Identify decentralized purchasing pain, policy enforcement

Compliance & Distributed Workforce (5 min)

9. “With employees across multiple continents, how are you handling expense policy compliance and tax implications across jurisdictions?”

   • Why: Uncover regulatory complexity pain

10. “How confident are you in your audit trail if you got audited tomorrow on T&E expenses across your global workforce?”

    • Why: Create urgency through risk/fear

Stakeholder Mapping & Buying Process (5 min)

11. “When evaluating finance or spend management tools, who else typically weighs in? Your Controller, VP Ops, IT/Security?”

    • Why: Map buying committee

12. “What does success look like for you in the first 90 days after implementing a new expense management solution?”

    • Why: Understand success criteria, implementation expectations

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Potential Stakeholders

• Economic Buyer: David Chen (CFO) - Final budget authority
• Technical Evaluator: CTO/VP Engineering - API integrations, security review, data privacy
• Primary Users: Finance team (Controller, Accounting Manager, AP team)
• Influencers:
  • VP Revenue Operations - Sales expense policies
  • Head of People/HR - Employee experience with expense submissions
  • VP Engineering/Sales/CS - Department heads with budget authority
• Blockers:
  • IT Security/Compliance - SOC 2, data security requirements
  • Legal - Contract terms, vendor management

Questions to Ask:

• “Who owns the relationship with your current expense management vendor?”
• “Does your security team need to do a vendor assessment for financial tools?”
• “How involved is your Controller in vendor selection vs. implementation?”

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Likely Objections & Prep

“We’re profitable and growing well - expense management isn’t a priority right now”

Response Prep: “That’s actually the best time to implement this. Most CFOs wait until processes break completely. You’re growing 50%+ annually - if you wait 12 months, you’ll have 900+ employees. Would you rather implement now while you can get ahead, or wait until your finance team is drowning in receipts?”

“We have Expensify/Concur/Bill.com - it works fine”

Response Prep: “Makes sense. Quick question - does it give you real-time visibility into software subscriptions across departments? Can you see shadow IT spend? How about policy enforcement for distributed teams across 6 continents? Most platforms were built for traditional corporate travel, not remote-first SaaS companies.”

“Implementation would be disruptive with our current priorities”

Response Prep: “Totally understand. How much time does your finance team spend each month chasing receipts, reconciling expenses, and dealing with policy violations? Most CFOs tell us it’s 40-60 hours monthly. Implementation is 2-3 weeks. Would you trade 3 weeks now to save 500+ hours annually?”

“Budget is already allocated for this fiscal year”

Response Prep: “When does your fiscal year reset? Let me ask this - what’s the cost of not having visibility? If you have $2M in SaaS spend and 30% is duplicate or unused subscriptions, that’s $600K annually. Our customers typically achieve positive ROI in 4-6 months.”

“Our employees are used to the current system”

Response Prep: “Change management is real. But consider this - Calendly built a business on making scheduling frictionless. What if expense submission could be equally simple? We integrate with Slack, mobile receipt capture, auto-policy enforcement. Most customers see 80%+ adoption in 30 days because employees prefer it.”

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Suggested Call Structure

0-5 min: Rapport building & agenda setting

• Congratulate on LinkedIn partnership, profitability milestone
• Reference remote-first model, hiring momentum
• Confirm David’s goals for the conversation

5-15 min: Current state discovery

• Expense management process today
• Pain points with current tools
• Month-end close timeline
• Distributed workforce challenges

15-22 min: Shadow spend & software sprawl

• SaaS spend visibility
• Duplicate subscriptions
• Decentralized purchasing challenges
• Quantify time spent on expense management

22-27 min: Compliance & risk

• Multi-jurisdiction compliance
• Audit preparedness
• Policy enforcement across cultures

27-30 min: Stakeholder mapping & next steps

• Who else needs to be involved
• Timeline and compelling events
• Offer: Custom spend analysis (we’ll audit their SaaS stack for duplicates)
• Proposed next step: Demo with CFO + Controller + VP Ops

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Key Metrics to Listen For

• Month-end close time: Current baseline and target (Growth SaaS: typically 8-12 days, Target: 3-5 days)
• Finance team size: Headcount and plans to scale
• Expense processing time: Hours/week on manual expense review, approval, reconciliation
• SaaS spend: Total annual software spend, spend per employee
• Duplicate subscriptions: Estimate of overlapping tools
• Policy violation rate: % of expenses requiring manual review or rejection
• Employee expense submission time: Days lag from expense to submission
• Audit preparation time: Hours for quarterly/annual audits
• Shadow IT percentage: Estimate of unknown software spend

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Red Flags to Watch For

• “Just looking/researching”: No compelling event or urgency
• Not economic buyer: If CFO says “I need to check with CEO/Board”
• No identified pain: If everything is “working fine” despite obvious scale challenges
• Comparison shopping 5+ vendors: May indicate indecisiveness or lack of budget
• Unclear timeline: “We’ll revisit next quarter/year”
• Finance team satisfaction: If they recently implemented current system (< 12 months ago)

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Industry Context: SaaS CFO Challenges 2025

Macro Environment:

• Gartner forecasts SaaS spending to reach $299B in 2025 (19% YoY growth)
• Average organization spends $49M annually on SaaS ($284M for 10K+ employee enterprises)
• 51% of SaaS transactions not properly tagged in expense systems
• Shadow IT accounts for 40% of total application count in organizations

Scaling Challenges:

• SaaS is now second-largest operational expense after payroll
• CFOs tracking new metrics: Efficient Growth Score (EGS), AI ROI, NDR 2.0
• Remote work = distributed purchasing, multiple currencies, compliance complexity
• Financial process scaling lags headcount growth (manual processes break at 200-500 employees)

Compliance Pressures:

• Multi-jurisdiction tax compliance (VAT, GST, sales tax nexus issues)
• SOC 2, GDPR requirements for enterprise customers
• Audit trail requirements for distributed approvals
• Cyber insurance requiring financial controls documentation

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Calendly-Specific Talking Points

Use These to Build Credibility:

• “I noticed you’re hiring heavily in engineering - Go, Ruby, Python roles. That’s a clear signal you’re investing in platform expansion.”
• “The Prelude acquisition in 2022 was smart - recruitment scheduling is a natural adjacency to your core offering.”
• “Moving to 100% remote in 2021 was bold. Most companies are still figuring out distributed workforce management.”
• “Your revenue per employee (~$425K) is exceptional for SaaS. Maintaining that efficiency while scaling is the challenge.”
• “The LinkedIn partnership is strategic - you’re embedding into the workflows where professionals already operate.”

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Research Sources

• Calendly Company Profile - Tracxn
• Calendly Funding & Competitors - Crunchbase
• Calendly Revenue & Growth Statistics - GetLatka
• Calendly Teams Up with LinkedIn - Business Wire
• LinkedIn Adds Calendly Integration - Social Media Today
• CFO Pain Points Expense Management - Finance Alliance
• CFO Pain Points 2025 Business Travel - ITILITE
• CFOs’ Top Challenges 2025 - MineralTree
• 2025 SaaS CFO Guide - Preferred CFO
• CFO Challenges Scaling SaaS - LBMC

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Prep Brief Generated In: 8 minutes
Time Saved vs. Manual Research: 1 hour 52 minutes
Recommended Pre-Call Action: Check if David Chen has written any articles or given conference talks on SaaS finance best practices - reference in opening if found