CEO Trips
The Deals, Ideas, and Friendships That Happen Off-Site
Some of the most valuable SIC connections have formed not in conference halls, but in airport lounges, resort evenings, and shared hotel corridors. CEO Trips are exclusive travel experiences for SIC founders — combining business exposure, meaningful networking, and the kind of time together that accelerates real trust.
There is a category of conversation that only happens when you are somewhere other than your office city. The combination of unfamiliar environment, unscheduled time, shared meals, and physical proximity over multiple days creates a trust depth that formal networking events cannot approach regardless of how well they are designed. SIC's CEO trips — both domestic retreats and international study tours — are built on this principle. The format is not incentive travel. It is structured informal relationship building over 3–5 days with a group of peers who have context about your business, your challenges, and your ambitions.
Domestic retreats to locations like Goa and Coorg are structured around a mix of facilitated sessions and genuinely free time. Facilitated sessions cover themes decided by the attending group — past retreats have covered questions like "what would you do if your top client left tomorrow," "how are you thinking about AI's impact on your headcount over the next three years," and "what is the one decision you keep deferring that you know you need to make." These conversations happen at a depth that a 45-minute conference session never reaches, because everyone in the room has skin in the same game.
International trips to Dubai, Singapore, and Malaysia serve a dual purpose: relationship deepening and market exposure. Itineraries include visits to technology parks, meetings with Indian diaspora business leaders who have built international companies, and structured market assessment sessions for founders considering international expansion. SIC trip participants have returned from Dubai with agency agreements, from Singapore with partnership MOUs, and from Malaysia with clarity about which international markets are realistic for their specific business model and which are not.
Trip cohorts are intentionally capped at 20–25 CEOs to maintain the intimacy that makes the format valuable. Larger groups fragment into sub-groups and lose the shared-experience quality that defines the best trips. Application for each trip is open to all SIC members, with selection based on balanced representation across company sizes, industries, and tenure in the community. First-time trip participants consistently rate the experience as the single highest-value SIC activity they have participated in, regardless of what individual sessions or events they have attended previously.
Goals
What this initiative aims to achieve
How It Works
Your path to participating
Annual CEO Retreat (Domestic)
A 2–3 day retreat to a resort or hill station — combining structured roundtable discussions with unstructured time. Past trips include Goa and Kerala. Limited to 20–30 founders.
International Business Exposure Trip
Organized visits to tech hubs in Dubai, Singapore, or Southeast Asia. Includes arranged meetings with local entrepreneurs, co-working spaces, and startup ecosystems.
Conference Travel Groups
SIC organizes group travel to major conferences — NASSCOM Product Conclave, TiECon, SaaStr, and others. Going as a community group means you network as a community.
Informal City Visits
Weekend trips to Bangalore, Mumbai, or Pune — visiting successful IT companies, incubators, and informal dinners with founders from other cities.
Action Checklist
Six steps to get maximum value
Apply for the next trip as soon as applications open
Spots fill within 48–72 hours of announcement — set a calendar reminder for the next trip application window
Prepare a one-page business brief before international trips
Describe your company, your target market, and one specific international opportunity you want to explore — this brief guides productive conversations during the trip
Come without a work laptop if possible
Delegates who try to work during trips get significantly less from them — inform your team you are unreachable and commit to being present
Take initiative in facilitating peer sessions
Volunteer to lead one session on a topic where you have hard-won experience — teaching peers accelerates your own clarity on the subject
Follow up with every trip participant within two weeks of returning
Trip relationships have a decay curve — a quick personal note referencing a specific conversation keeps the connection warm
Document one business decision you will make because of the trip
Write it down on the last day of the trip and share it with the group — accountability increases follow-through
Key Benefits
What you gain from participating
"The Singapore trip changed the trajectory of my company. I went expecting to see technology parks and came back with a referral partnership with a Singapore-based managed services firm that needed Indian development capacity. That partnership brought us ₹48 lakh in revenue in year one. But more than the business outcome, the five days with 20 other Surat founders gave me a peer group I talk to every week. You cannot build that in an office."
Dhaval Chauhan
Volunteer, Surat IT Community
How to Participate
CEO Trips are exclusively for SIC member founders and senior leaders (co-founder, CTO, COO). Seats are limited and filled quickly. Watch for trip announcements in the SIC community group — registration opens 6–8 weeks in advance.
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