When does it make sense to fly to a customer mid-deal?

Only if: (1) deal is >$500K, (2) you've hit a real objection that requires your presence (not just checking in), or (3) the customer asked for it. A site visit is a signal; don't show up uninvited or you'll look desperate. The visit should change the deal trajectory.

Site Visits: When They Matter

Flying out is expensive and time-consuming. Don't do it for face time—do it to move a deal.

WHEN TO FLY (4 valid reasons):

1. Deal is stalled on a real objection you can unblock in person

• Stall: "We need to see how it integrates with our legacy system"
• In-person: You bring your CTO, meet their VP Eng, whiteboard the integration
• Result: Technical concern moves from blocker to solved

1. Deal size justifies it (>$500K or strategic account)

• $500K deal: 1-day trip, ROI is high
• $100K deal: Don't fly (Zoom is fine)

1. Customer explicitly asked for it

• "We'd like to meet your team and see how you work"
• This is a signal they're serious and checking you out
• Action: Bring relevant team (AE + success manager or CTO if needed)

1. Deal is in final negotiation and relationship needs anchoring

• You're on the 1-yard line, CFO wants to meet you
• Quick trip, confirm partnership mindset, close
• High ROI because deal is already 90% done

WHEN NOT TO FLY (very common mistakes):

• Deal is early stage (week 2-4 of discovery) → Zoom is fine
• Objection is price/ROI → fly doesn't fix that, conversation does
• "Show confidence" → flies signal panic, not confidence
• "Build relationship" → good relationships happen on Zoom with good outcomes
• You're checking in ("no reason, just wanted to connect") → don't

THE SITE VISIT PLAN (if you do go):

1. Set clear agenda

• "I'm coming to meet your team, whiteboard the integration, and confirm next steps."
• Not: "Let's meet and see where we are."

1. Bring the right person

• If technical issue: bring your CTO or engineer
• If sales/ROI: AE + success manager
• If both: AE + tech lead + CS lead (3 people max)

1. Plan 4-6 hours max

• Not a full day (too much time, signals desperation)
• Typical: 2-hour meeting + 1-hour individual conversations + buffer

1. Go in to unblock something

• Whiteboard the integration
• Walk through their security requirements
• Confirm implementation timeline with their ops team
• Final negotiation on terms (if near close)

1. Leave with a clear next step

• Not: "Thanks for the meeting"
• Yes: "Based on our conversation, here's what I'm committing to [X], you're committing to [Y], and we'll close by [date]."

COST vs BENEFIT:

RED FLAGS (don't fly):

• Customer hasn't asked for it, rep wants to "build relationship"
• Deal is only at 40% conviction (too early)
• Objection is something Zoom can solve ("show me the integration")
• You've already visited and nothing has changed (don't revisit)

TIMING: Best time: Week 8-12 of a deal (after discovery, before legal). Early enough to fix issues, late enough they're seriously buying.

REMOTE ALTERNATIVE (often better than flying):

• Live screen-share whiteboard session (1 hour, you + their tech + your CTO)
• Closes 80% of technical questions
• Costs $0
• If they still want to meet after that, fly then

THE ONE RULE: If you can solve the objection over Zoom, do it. Fly only if in-person presence changes the outcome.

TAGS: customer-visits, deal-stage, travel-strategy, relationship-building, cost-efficiency