How To Plan A Great Offsite For Sales, Marketing, and Go-To-Market Teams
Recently, GTM Partners wrote about their "7 Rules for a Good GTM Offsite" and we build on their ideas below...
Yesterday, I attended a conference called GTM Is Better Together hosted by a firm called GTM Partners.
In the room were People Leaders, as well as CROs and VPs/SVP of Sales, from a wide variety of startups like G2, Clari, and Vidyard as well as larger companies like Cisco, Equifax, and Fiserv.
Among the many topics of conversation was how to engage and align various teams (marketing, sales, operations, customer success, product, etc) for more effective GTM campaigns.
Given many companies are remote or hybrid, offsites are increasingly utilized as a tool for facilitating crucial cross-department collaboration and getting everyone bought into the same vision.
Sangram Vajre, CEO of GTM Partners was previously CMO of Pardot, then co-founder of Terminus as well as a WSJ bestselling author on GTM strategy, wrote about planning offsites for GTM teams only a couple weeks before we connected via Pavilion (article below), and today I wanted to examine some of his “pro-tips” to share how you can apply these ideas to your own upcoming offsites.
GTM Partner’s “7 Rules” And Ideas For Implementing Them At Your Own Offsites
As the founder/CEO of Offsite, I’ve overseen hundreds of offsites that our team has planned for companies like Buffer, Reforge, 15Five, Remote, Guild Education, and others backed by the YC’s, a16z’s, Sequoia’s, and other top venture firms of the world.
We provide end-to-end offsite planning services for these companies, where we take care of all logistics while also advising on agenda creation, budget management, and creation of a higher ROI event based around a company/team’s business objectives for any given offsite.
We also offer an Airbnb-style marketplace where you can easily book your offsite venue with us to save up to 40% on room blocks, meeting space, F&B, and more, as well as other offsite vendors like travel providers, speakers, facilitators, swag, photographers, videographers, and more.
Below, I’ve quoted each of GTM Partners’ “7 Rules” and added my thoughts underneath so you can plan better offsites for your sales, marketing, and GTM teams.
1 - “The CEO must be in the room. At the end of the day, the CEO is the only one with the authority to make cross-functional decisions and is the true owner of GTM.”
For larger offsites like Sales Kickoffs, I agree with this entirely.
When you’re planning an offsite for your sales, marketing, or GTM teams and want to ensure that the brainstorms, trainings, debates, decisions made, and celebrations have lasting value, having your CEO (and other senior leadership) present will ensure better preparation ahead of the meeting, as well as greater follow-up from the meeting.
Companies who do this well in January or February (when most Sales Kickoffs occur) are much more likely to enjoy a high-growth year ahead, because they’ve created the conditions for success in their organization.
Better planning for an offsite ensures greater alignment across teams.
Employees leave the Sales Kickoff more engaged, and therefore stay at the company longer, allowing for more focus on “doing the work” than having to manage employee turnover, re-training staff, changing plans mid-year, etc.
2 - “All the functional heads must attend: Key players on the GTM team include sales, rev ops, marketing, product, and customer success.”
One of the benefits of a Sales Kickoff, and offsites for GTM teams in general, is cross-department collaboration. It’s easier to get “buy-in” across the board when everyone knows what the game-plan is, why they are doing what they’re doing, and how they will be managed moving forward.
As we work with Offsite clients, we help them think through how to program the offsites in order to build a compelling vision across the board.
We also take care of the logistics so our clients can focus on their “pre-work” and come better prepared to showcase their strategic plans for sales, rev ops, marketing, product, and/or customer success.
Every company is different, but for some of our favorite session ideas during Sales Kickoffs, check out our 2025 Sales Kickoff Agenda Template.
This template can apply to other sales or marketing-team meetings as well. Check it out and let me know what you think.
3 - “Engage a skilled facilitator with no stake in the game. A neutral, independent, impartial third-party should facilitate to ensure all voices are heard. They focus on the process, not the content. When a CEO is the facilitator, it can dampen participation, discourage disagreement and make the CEO choose between leading the team and keeping the meeting on track.”
This is a great idea for any offsite.
When you have invested a lot of money, as well as your team’s time, into an offsite, you want to ensure the ROI from those meetings is high.
A great facilitator can enhance any offsite, teach attendees something new, and assist a CEO, team leader, Head of People, and/or Chief of Staff in driving the desired business outcomes of a team retreat.
Not all facilitators are created equal, though.
As a former TED and TEDx speaker myself, who worked with various executive teams in the Fortune 1000 as an outside facilitator, I was fortunate enough to join groups like the National Speakers Association early in my career.
I learned there are many highly skilled speakers and facilitators in the world, but there are also 10 times as many rookies and newcomers looking to change careers, and potentially use your company as their testing grounds for unproven facilitation practices.
You don’t want to gamble with this resource, should you bring in outside speakers or facilitators.
Offsite can help you find vetted options for keynote speakers and facilitators based on your budget, desired experience, and more. Let us know what you’re looking for here and we’ll follow up ASAP with a shortlist of options for you to consider.
4 - “Identify desired outcomes before the meeting starts. What decisions do you hope will get made? What are the most important objectives for the meeting?”
There are many different business objectives you can accomplish during an offsite. You can even create an agenda to accomplish multiple objectives, but you can’t do everything with limited time and budget.
We recommend sending pre-offsite feedback forms to your team in order to figure out what would make for an engaging and valuable meeting to attendees. Then, think through what you’d like to accomplish in the offsite as a team leader, and create an effective agenda, budget, and overall experience from there.
Some resources you might find helpful to dive deeper when planning your next sales, marketing, or GTM offsites:
5 - “Select the right location. Choose a location that will foster productivity and creativity. It should be comfortable, free from distractions, and provide necessary facilities for meetings and activities. It should also be accessible to all participants, considering factors like travel. Most importantly, it should be offsite! Don’t attempt to do this work in your regular office or on Zoom.”
When determining how to build software that could make team retreat planning easier, the Offsite team started with venue selection.
Where you have your offsite is one of the most consequential decisions you’ll make regarding your budget, use of attendee’s time, and overall attendee experience.
We’ve created an Airbnb-style marketplace with over 1000 premier offsite venues globally, at which you’ll save up to 40% on room blocks, meeting space, F&B, activities, and more.
We are adding other vendors into our marketplace over the coming quarters, including but not limited to: travel providers (flights, travel visas, on-the-ground transport), speakers, facilitators, swag, photographers, videographers, activity providers, event production staff, day-of coordinators, and more. Let us know here if you need help with any of these vendors and we’ll be happy to source options for you!
6 - “Give your schedule some breathing room. An offsite should include learning, participation, collaboration, and some team building time.”
We like to add “Flex Time” to our agenda, which can be used in emergencies if sessions are running over on time.
It also gives attendees space to get work done, call their family, take a nap, workout, meet a friend, or have unstructured social time with colleagues (which is a vital part of any offsite).
Don’t forget to plan some fun activities during your offsite to let everyone blow off steam and enjoy unique shared experiences together.
That’s where real trust and teambuilding occurs.
7 - “Ensure effective follow up. The best offsite can be sunk if it doesn’t result in any changes. Set expectations before the offsite for regular check-ins to stay on track or make adjustments throughout the year.”
Right now, most companies (including yours, perhaps) have no strategy around planning offsites or team retreats.
Many People Leaders responsible for planning offsites get stuck in a vicious cycle of convincing their CEOs/Founders to plan team retreats, then waste valuable time going back-and-forth on everything from budget to destinations to agenda, only to be left with limited time to plan an offsite.
Still, the ROI from these offsites ends up being quite high, leading to a commitment for future offsites, only to repeat this cycle by department with each quarter and each year.
Just like you need a rhythm of business to run the company, or a GTM strategy to ensure you fill your pipeline, you need a predictable offsite cadence.
With 2025 approaching, you might be evaluating your offsite plans for next year. What is the optimal offsite cadence to keep your team(s) aligned, motivated, and adaptable to the ever-changing business climate?
When should you plan your Sales Kickoff, President’s Clubs, company All-Hands, and other team retreats?
I wrote about “The Cadence” here, so you can see what pioneers like Dropbox, GitLab, and Airbnb do for their retreats. Of course, if you reach out to jared@offsite.com with questions about your specific needs, I’m happy to help as well.
Planning A Sales Kickoff, or some other GTM offsite?
We’d love to help!
Again, you can start by making a free account at offsite.com to search our marketplace of 1000+ offsite venues globally.
You can also book a discovery call to talk through our end-to-end retreat planning services, trusted by hundreds of highly-rated employers and high-growth companies who leverage our experience to plan higher ROI offsites.
If you’re a fan of GTM Partners and want their input on upcoming offsites, I’ve been chatting through ways Offsite and GTM Partners can partner up to provide the best content, facilitation, environment, and logistics for Sales Kickoffs and other type of offsites.
If you’d like to work with both companies at the same time for this purpose, email me at jared@offsite.com and I’m happy to share some of our initial thoughts on how Offsite and GTM Partners can collaborate to provide you the best possible GTM offsites.