SaaStr AI Annual 2027 travel guide: Hotels, flights, and attendee tips

Produced by SaaStr, SaaStr AI Annual brings together B2B SaaS and AI founders, executives, operators, and investors for two days of workshops, executive summits, exhibits, and networking. Planning ahead can help you make better use of your time and return with relevant insights, new contacts, and clear next steps.

What is SaaStr AI Annual and who is it for?

SaaStr AI Annual is a B2B SaaS and AI event produced by SaaStr, which was founded by Jason Lemkin. The 2027 event will bring founders, executives, operators, and venture capitalists to the San Mateo County Event Center in San Mateo, California.^[1]

Attendees include startup founders, chief revenue officers (CROs), chief marketing officers (CMOs), chief customer officers (CCOs), sales and marketing professionals, product leaders, and investors. They come to explore AI and go-to-market strategies, attend workshops and executive summits, evaluate products and potential partners, meet with investors, and connect with others across the B2B SaaS industry.

The organizer expects at least 10,000 attendees, hundreds of speakers and roundtables, dozens of workshops, and at least 1,000 scheduled one-on-one meetings at SaaStr AI Annual 2027.^[1][6] These figures provide a useful sense of the event’s anticipated scale for 2027.

What makes SaaStr AI Annual 2027 worth the trip

SaaStr AI Annual gives attendees opportunities to discuss B2B SaaS and AI strategies with experienced operators, meet potential investors and partners, compare products, and build relationships through scheduled meetings. The detailed 2027 agenda hasn’t been published, but SaaStr says the two-day event will include at least 50 hours of content, executive summits, workshops, roundtables, and networking programs.[6]

Here are some of the experiences you can expect:

• Who Do You Want to Meet: SaaStr’s matchmaking app schedules one-on-one meetings based on attendees’ interests. Identify your highest-priority contacts and reserve time for these meetings once scheduling opens.^[1][6]
• Workshops and roundtables: Attend expert-led workshops and interactive roundtables covering AI, go-to-market strategies, sales, marketing, customer success, and product development. SaaStr says roundtables will be capped at 20 participants to support conversation between speakers and attendees.^[6]
• Executive summits: Dedicated CMO, CRO, and CCO summits will bring senior leaders together for role-specific programming and discussions. Participation may require a separate application or approval.^[1]
• Speakers and educational sessions: SaaStr expects hundreds of speakers from B2B and AI companies. Check the official agenda once it’s published for confirmed speakers, session topics, and times.^[1][6]
• Funding opportunities: Founders can apply for Meet a VC, connect with other founders and executives at similar company stages, and potentially pitch their startups through the event’s pitch competition.^[6]
• Side events: SaaStr plans happy hours, dinners, brunches, and after-parties across the San Francisco Bay Area. Review each location carefully and avoid overbooking your evenings before the conference schedule is available.^[1]

Where to stay for SaaStr AI Annual 2027

Choosing the right hotel can simplify transportation to the San Mateo County Event Center, especially with scheduled meetings, workshops, and other programming concentrated into two days. Hotels near the venue provide the shortest trip, while downtown San Mateo, Foster City, and Belmont may offer more dining options or lower rates.

Hotels by distance to the San Mateo County Event Center

Compare these areas by estimated driving time, transportation access, and current rates. Travel times are approximate and can vary with traffic, the hotel’s exact location, and the entrance you use.

Staying near the Event Center or Hillsdale may make it easier to arrive on time and return to your room between commitments. Downtown San Mateo provides more restaurants and evening options, while Foster City and Belmont expand the selection of business hotels within a relatively short drive.

Hotel pricing at SaaStr AI Annual 2027

Navan analyzed anonymized hotel bookings in San Mateo and Foster City during the dates surrounding SaaStr AI Annual 2026.^[3] The figures provide context for planning a 2027 trip, but they don’t predict rates during SaaStr AI Annual 2027.

• Median hotel rate: The median nightly rate during the analyzed period was $324, compared with $287 during a mid-April comparison period.^[3]
• Stay length: Business travelers booked an average stay of 2.8 nights.^[3]
• Late bookings: Approximately 41% of stays were booked within two weeks of arrival.^[3]
• Booking window: The highest median nightly rate was $345 for bookings made two to four weeks ahead. Median rates ranged from $312 to $331 across the other booking windows, but differences in hotel availability and room type mean travelers shouldn’t assume that waiting will produce a lower rate.^[3]

SaaStr says it has secured rates at nearby hotels for the 2027 event.^[8] Use the hotel link provided through the official SaaStr AI Annual website, and compare room-block rates, cancellation policies, and transportation time before booking. Staying in downtown San Francisco generally requires a much longer trip to the San Mateo venue.

San Francisco flight trends

San Francisco International Airport (SFO) is the primary airport for travelers attending events in San Mateo.^[5] Navan flight data for SaaStr week 2026 includes 2,406 business travel bookings to San Francisco, with 19.6% originating outside the U.S.^[3] The most common origin locations were New York, Seattle, Newark, Chicago, and Boston.

Travelers coming from the East Coast or other distant locations may want to arrive Monday, May 10, rather than travel on the first day of the event. This provides time to reach the hotel, prepare for scheduled meetings, and account for potential flight or ground transportation delays.

How Navan Edge helps you book your conference travel

Navan Edge, your personal travel assistant powered by AI and supported 24/7 by human travel experts, can plan and book your SaaStr AI Annual 2027 trip. Tell Navan Edge what you’re looking for, and it can compare flights, hotels, and restaurants using live availability, personal preferences, and the amenities that are important to you. Then, book everything in the same conversation without juggling multiple apps or websites.

Continue earning your usual airline miles and hotel loyalty points, earn credit card points, and get an additional 5% back in Amazon Gift Cards on eligible hotel stays. See our travel rewards on business trips guide for a closer look at how it works.

Set your San Mateo budget before traveling

Plan your SaaStr AI Annual 2027 budget around registration, lodging, transportation, meals, and other travel expenses. Staying close to the San Mateo County Event Center may simplify your schedule, but hotel rates can exceed your company’s usual lodging allowance.

Federal per diem for San Mateo

The U.S. General Services Administration sets federal per diem rates for lodging, meals, and incidental expenses. These rates apply to federal employees traveling on official business, although some companies also use them as benchmarks when setting travel budgets and reimbursement limits.

For SaaStr AI Annual 2027, the FY2027 rates for San Mateo and San Mateo County are:

• $280 per day combined: Includes $194 for nightly lodging plus $86 for daily meals and incidental expenses (M&IE)^[4]
• M&IE breakdown: Includes $22 for breakfast, $23 for lunch, $36 for dinner, and $5 for incidentals^[4]
• First and last travel days: Includes an M&IE allowance of $64.50, or 75% of the daily M&IE rate^[4]

The $194 federal lodging allowance is $130 lower than the $324 median nightly rate in Navan’s 2026 SaaStr-week hotel data.^[3][4] If your company uses GSA rates as a benchmark, compare hotels in downtown San Mateo, Foster City, and Belmont and account for additional transportation costs before choosing a lower nightly rate.

Other expenses to consider

Planning for these expenses before you book can make it easier to set a realistic budget and avoid surprises when submitting your expense report.

• Conference registration: Early-bird tickets currently cost $1,099 for startups with less than $20 million in annual recurring revenue (ARR) and $1,399 for large companies and venture capitalists. Team rates are $799 and $1,099 per person, respectively, with a minimum purchase of three tickets. The current offers are scheduled to end Sept. 30, 2026.^[6]
• Hotel taxes and fees: Lodging taxes, parking charges, deposits, and cancellation policies vary by hotel. Compare the total stay cost rather than the advertised nightly rate.
• Airport transportation: Budget for a taxi, rideshare, or public transit between SFO and your hotel. Travelers using public transit can take BART to Millbrae and transfer to Caltrain, but should check schedules and account for the final trip from Hillsdale Station.^[5][7]
• Meals and business dinners: Budget for meals that aren’t provided by the conference, including dinners with customers, founders, investors, or colleagues. Reserve tables early if you’re coordinating a larger group.
• Local transportation: If you stay outside the immediate Event Center area, include rideshare, taxi, public transit, or parking costs in your budget.
• After-hours networking: SaaStr plans dinners, happy hours, brunches, and other side events across the San Francisco Bay Area. Leave room for additional transportation and meal costs until locations and schedules are confirmed.^[1]
• Extended stay: If you depart Thursday, May 13, include the additional Wednesday-night hotel stay and related meal costs in your budget.

Plan your SaaStr AI Annual agenda

The SaaStr AI Annual 2027 session schedule, speaker lineup, workshop and roundtable times, matchmaking schedule, badge pickup hours, and detailed side-event calendar haven’t been published. SaaStr has confirmed that the two-day event will include workshops, executive summits, roundtables, scheduled one-on-one meetings, and at least 50 hours of content, but its current agenda page still features the 2026 program. Don’t use those session details to plan your 2027 trip.^[1][6]

Once the 2027 schedule becomes available, build your agenda around your highest-priority Who Do You Want to Meet appointments, workshops, roundtables, and speakers. Leave time for exhibits and unscheduled conversations, and check whether executive summits or funding programs require separate applications.

Confirm the opening and closing times before finalizing your flights, and use our business trip planning guide to coordinate your travel plans around the event schedule.

What to pack and wear at SaaStr AI Annual

SaaStr attendees generally wear business casual clothing. Plan on jeans or slacks, collared shirts, blouses, sweaters, and comfortable shoes. Consider bringing a blazer or another polished option for investor meetings, customer dinners, and evening events.

May weather can vary across the Bay Area, so check the forecast before you pack. Bring layers that are easy to add or remove as you move between cool meeting rooms and outdoor areas around the San Mateo County Event Center.^[10]

Conference essentials

A few practical items can make two days of sessions, workshops, meetings, and networking more comfortable. Add these essentials to your packing list:

• Two pairs of comfortable shoes: Rotating shoes can help reduce fatigue when you’re moving between sessions and scheduled meetings.
• Portable charger: The event app, matchmaking messages, notes, and photos can quickly drain your phone’s battery.
• Reusable water bottle: Long indoor days and hours of conversation make it important to drink water regularly.
• Throat lozenges and hand sanitizer: Crowded event spaces and extended conversations can take a toll.
• Light sweater or jacket: Meeting rooms may feel considerably cooler than the temperature outside.
• Small backpack or laptop bag: Carry your charger, water bottle, meeting materials, and other essentials comfortably.

Getting from the airport to the SaaStr venue

San Francisco International Airport (SFO) is approximately 10 miles from the San Mateo County Event Center and is the primary airport for most attendees.^[5] Badge pickup and opening hours for 2027 haven’t been published, so confirm the schedule before booking your flight. For most travelers, arriving Monday, May 10, should provide time to check in before the event begins Tuesday.

For travelers with luggage, a rideshare or taxi is generally the simplest way to reach a hotel in San Mateo, Foster City, or Belmont. Public transit offers an alternative but requires a transfer from BART to Caltrain at Millbrae and may require a final walk or rideshare from Hillsdale Station.

Traffic, airport congestion, train schedules, and transfer times can increase travel times. SFO’s free AirTrain connects all terminals with the airport BART station, rental car center, and parking facilities.^[13]

Beyond sessions: Make time for meetings and networking

SaaStr AI Annual combines educational programming with Who Do You Want to Meet appointments, workshops, roundtables, funding programs, and informal networking. The 2027 matchmaking timeline, event app, floor plan, and detailed operating hours haven’t been published. Wait for those details before assigning meetings or activities to specific times and locations.

• Complete the matchmaking process: Once Who Do You Want to Meet opens, follow each selection and scheduling step by the organizer’s deadlines.
• Prioritize relevant contacts: Identify founders, operators, investors, customers, and potential partners connected to your current goals rather than trying to meet as many people as possible.
• Apply for funding programs: Founders interested in Meet a VC or the pitch competition should check eligibility requirements and application deadlines once SaaStr publishes them.
• Use workshops and roundtables strategically: Choose programming connected to current business challenges, and leave time afterward for conversations with speakers and other attendees. SaaStr says its expert-led roundtables will be capped at 20 participants.^[6]
• Schedule additional meetings: Contact customers, partners, investors, and colleagues about two weeks before the event to arrange coffee chats or other meetings outside the matchmaking program.
• Use the event app: Once the 2027 app becomes available, use it to manage appointments, save sessions, review schedule changes, and navigate the venue.
• Take notes after each conversation: Record relevant details, questions, contacts, and agreed-upon next steps while the discussion is still fresh.
• Follow up within 48 hours: Send a brief email or LinkedIn message that references the conversation and confirms the next action.
• Build in short breaks: Two days of sessions, meetings, and networking can be tiring. Leave time to eat, drink water, organize your notes, and recharge between commitments.

What to eat at SaaStr AI Annual 2027

SaaStr hasn’t confirmed whether 2027 registration will include meals. Check the agenda and ticket details once the meal schedule is published, and keep a snack in your bag for periods when workshops, roundtables, and scheduled meetings leave little time to eat.

When it’s time for a client dinner, team meal, or quick lunch, these options are convenient to the San Mateo County Event Center:

• Client dinner: San Mateo Prime at 174 E. Third Ave. offers a steakhouse setting in downtown San Mateo. Reserve ahead if you’re planning a customer, investor, or partner dinner.^[9]
• Team meal: Downtown San Mateo and 25th Avenue offer several restaurants suitable for groups within a short drive of the Event Center. Compare menus, availability, and group policies before choosing.^[8]
• Quick lunch: Hillsdale Shopping Center and Park Place at Bay Meadows offer several counter-service and casual options near the venue when you don’t have time for a full meal.^[2]

Restaurants and operating hours may change before May 2027, so check current information when making reservations. Navan Edge can book San Mateo restaurants in the same chat where you arrange your flight and hotel.

Finish strong on departure day

Before you check out, take a few minutes to organize your receipts, notes, and new contacts so you’re not sorting through everything after you return home. Allow enough time to reach SFO, check your bags, and clear security before your flight.

• Pack the night before: Charge your devices, organize your receipts and notes, and check the room for chargers, badges, and other belongings.
• Confirm late checkout: If you have an afternoon or evening flight, ask the front desk about late checkout or have Navan Edge coordinate the request on your behalf.
• Arrive early at the airport: Traffic on U.S. 101 and congestion at SFO can add time, so allow at least two hours for a domestic flight and three hours for an international departure.
• Submit expenses early: Upload receipts while hotel, meal, and transportation charges are still easy to identify, following your company’s expense policy.
• Begin your follow-ups: Use time at the airport or on your return trip to organize contacts and send brief messages confirming agreed-upon next steps.
• Schedule a debrief: Block time early the following week to share relevant findings, review potential partners or investments, and decide which ideas or conversations require further action.

Make the most of your SaaStr AI Annual 2027 trip

SaaStr AI Annual brings thousands of B2B SaaS and AI founders, executives, operators, and investors together for two days of sessions, workshops, roundtables, meetings, and networking. Register and book your hotel early, set clear priorities for the trip, and revisit your plans as the 2027 agenda and Who Do You Want to Meet schedule become available.

Planning your SaaStr AI Annual 2027 trip? Let Navan Edge line up SFO flights, Peninsula hotels, and founder dinners in one thread.

Navan is not affiliated with, endorsed by, or sponsored by SaaStr AI or their organizers, and this guide is not an official SaaStr publication. SaaStr and all other third-party trademarks referenced herein are the property of their respective owners and are used for identification and descriptive purposes only. All schedules, pricing, venue details, and program information are subject to change; verify current details with the official organizers before you travel.

Navan publishes this guide as part of its Navan Edge content series. Navan Edge is a Navan product referenced throughout this post. Card benefits, fees, loyalty program thresholds, earning structures, reward values, and AI capabilities described in this article are subject to change and were accurate as of the date of publication. Verify current terms with your card issuer, loyalty program operator, or the relevant program’s website before making decisions. Amazon Gift Card rewards are subject to Navan Edge Terms and Conditions for eligible hotel bookings.

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