Smarter Discovery Questions to Engage VP Finance in Tech/SaaS
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Summary:
For a VP Finance in a high-growth tech company, the focus is on cost visibility, cash flow optimization, compliance, and enabling strategic decisions. The right discovery questions will uncover their current financial blind spots, operational inefficiencies, and priorities helping you position your spend management solution as a critical enabler.
Here’s a library of 30 strategic discovery questions, designed to guide your early conversations and align with their goals.
1. Financial Visibility and Control
- How confident are you in your ability to track company spend in real-time?
- Where do you see the biggest gaps in spend visibility today?
- Are there areas where spend tends to go unnoticed until it’s too late?
- What’s your current process for approving or flagging large expenses?
- How much manual effort is involved in reconciling spend across teams?
2. Policy Compliance and Risk Management
- How do you ensure company-wide compliance with your spend policies?
- Are there recurring audit issues or exceptions that frustrate your team?
- What challenges do you face in enforcing procurement and expense policies?
- How are you currently managing vendor-related risks?
- Has spend leakage or fraud ever been a concern for you?
3. Budgeting and Forecasting Accuracy
- How accurate are your current spend forecasts across departments?
- What’s the biggest bottleneck in aligning budgets to actual spend?
- How do you evaluate whether each department’s spend is driving ROI?
- Are you able to adjust budgets dynamically based on changing business needs?
- How do you currently collaborate with department heads on budgeting decisions?
4. Operational Efficiency and Scaling
- What finance processes are still heavily manual or spreadsheet-based?
- How do you balance governance with the need for team agility on spend?
- Are there repetitive workflows you wish you could automate?
- How do you ensure your finance function scales efficiently with company growth?
- Where do you see opportunities to simplify your spend management processes?
5. Strategic Finance and Business Impact
- What financial insights would make the biggest impact on your decision-making?
- How well are spend patterns aligned with your company’s growth priorities?
- What KPIs are you most focused on improving this year?
- How do you evaluate tools or solutions for driving financial efficiency?
- What’s the cost to your team of not solving current spend challenges?
6. Vendor and SaaS Spend Optimization
- How do you currently track and manage SaaS subscriptions across teams?
- Are you confident you’re getting the best terms from key vendors?
- How often do you renegotiate or rationalize vendor contracts?
- Has SaaS sprawl become a challenge in your organization?
- What would a 5% reduction in total vendor spend mean for your budget this year?
How Pepsales AI Helps
Pepsales AI helps sales teams ask the right questions, faster. It delivers intelligent, role-specific, and industry-aware discovery questions in real time tailored to the context of each deal.
What it delivers:
- A library of proven questions per industry, persona, and product
- Smart prompts that adapt to buyer role, objections, and stage
- Embedded coaching and insights to guide better conversations
- Automation of discovery prep, no more guesswork
Whether you’re prepping for a demo or coaching new reps, Pepsales AI ensures every conversation starts strong and gets to the real need, fast.
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