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Hey Sifted Reader,

When your team is fully (or partly) based all over the place, getting some rare in-person time together can be super valuable. So this week, we're delving into the growing trend of offsites — how do you run a good one, what’s the point of them, what do you do once you’re there and more.

See you next week,
 Amy and Anisah 🧡

\How to

Run an offsite

When we asked Twitter a while ago who ran great offsites, Elisa Rueda’s name popped up. She is the founder of The Cowork Experience — a company that creates and manages team offsites and provides online programmes for team growth and development. She’s been trusted by the likes of open source platform GitLab, investor platform and jobs board AngelList and consultancy Capgemini. She’s taken teams everywhere from Hawaii to Bali. We got her top tips for running an effective offsite for your team:

Determine how long you need. A lot depends on the size of your team: a company-wide offsite for 100 to 150 people normally lasts three days and three nights. When you're hauling so many people around, you need to plan in logistics time. If your company is smaller or you’re taking out a group (a particular department or the executive suite), a shorter stay can be just as effective. 

Run offsites more often. Prior to the pandemic, offsites gathered multiple offices of the same company in one place to meet. So once a year was probably enough. With remote-first companies, extra coworking time is valuable for team building, morale and team mental health — so a cadence of once a quarter may be better. The more you have, the more variety you need to make them fun and not feel like a chore. Maybe the first is a longer stay, the second only a night; one at the beach, one in the mountains, etc.  

Choose a location that meets your needs. Budget: go somewhere that gives your team an exceptional experience. If you have a smaller budget, choose an offsite location in your country to be able to do that. Safety: this is not just a holiday. You are responsible for your team so select somewhere that meets your health and safety, accessibility and code of conduct requirements. Time zone: part of the team will need to work so choose somewhere that works for the regions you are serving (and that has good wifi!).

Plan in work time and downtime. Your goal is to team build; if people are stressed about tasks not done or they’re too drained from back to back activities, you’ll miss people coming together naturally — which is what this is all for. So figure out how many hours people need to be working. Be explicit about the time you’re setting aside for it. Also, plan times where nothing is planned. Let them sit around, have a cup of coffee, relax and digest what they’ve been doing… meaningful conversations will happen in these moments. They will be the most valued times, not the most expensive activity. 

Set varied activities. You need to have choices in your agenda for all different types of personalities and interests. Forced fun is no fun. People need to feel comfortable for an offsite to be valuable. We always have: something with a wellness angle like yoga or meditation; a workout; a high impact sport; an intentional team activity — for example, on one offsite there was a cart building exercise; something fun and different like team Olympics; a big brain problem like a critical thinking maze. You’ll have already met many interests by providing one activity from each of these groups. 

Reassign what you’d spend on an office on offsites. Most offsite budgets are planned per person. If the location is farther away and flights required to get there are more expensive, you could be looking at $300 per person per day over three days. If you’re in the same country, $150 per person per day could do it.

\A message from our sponsor Zendesk

Bad CX could be losing you customers

Look after your customers — or your competitors will. Apply for Zendesk for Startups Program to get free advice and six months of customer support software.

Find out if you qualify here.


Enter the era of the “workcation”

Tempted to try working abroad but not sure where to begin? Well… there’s a startup that can help with that.

Smartway, which was founded last year, sells “workcation” packages in small Italian towns for companies to offer — for free — to their employees.

But why would any startup be so generous? Eleanor Warnock finds out.

\On The Subject Of...

Running offsites

🛠️ Team building activities. You've sorted the location, got your people there — what's next? Here's some inspiration to get you going. 

💻 Run a virtual offsite. If your team is based around the world, it may be too complicated (and expensive!) to get everyone together. So how do you run an effective remote get-together? 

📖 A framework for offsites. Claire Johnson, chief operating officer of Stripe, has put together this excellent toolkit to get you started.

🕴️ The need for executive offsites in a remote world. Checkout GitLab's open source breakdown of and learnings from its executive getaways. 

📦 Offsite in a box. This new toolkit has useful practical resources and guides for running an offsite — there is some particularly good stuff around strategy and brainstorming.

\Sifted Talks

Subscription models: Everyone’s got one, so how do you make a good one?

Our next Sifted Talks is all about subscriptions. Hear from founders across software, food and femtech on what it takes to build and implement one that stands out from the crowd. 

Register now and join us on December 1.

\People Moves

Lisa Rodwell has joined tampon startup Daye as CEO. Lisa, who we previously spoke to for Startup Life about non-exec board members, will work alongside Daye founder Valentina Milanova. 

Vakis Rigas is joining Rotterdam-based logistics startup Shypple as VP of marketing. Vakis was previously head of product marketing at Typeform. 

Shaun Sharkey will head up Crowdcube’s secondaries product. The idea is to give more founders and early-stage employees opportunities to sell some of their equity before their startup exits.

Got any people intel you'd like to share with us? We'd love to hear it... 😉 

\Smart Reads

1) Culture is everything. This podcast chats with founder and CEO of delivery service Bolt Ryan Breslow on the role of culture in the company’s success. 

2) Why you should join a board. Ex-head of Google Campus and serial board member Sarah Drinkwater outlines why ambitious and successful operators might want to take up a non-executive director position — and how to do it.

3) Lessons from running a startup. This is a great read on what a founder learnt through the journey of starting and fundraising for her company. 

4) Tech is impacting social mobility. This is worth reading just for the fun website experience but it's also a thought-provoking take on tech's role in the distribution of wealth and class systems.

5) What does web3 mean for communities? Will web3 be the innovation needed to make community first and profit sit more comfortably together?

Read something you think everyone else should too? Send it on over to Anisah.

Forwarded this newsletter?

Subscribe to Startup Life.

\Podcast of the Week

Mental Health at Work: Revolut

Come and take a seat on the therapy couch in this new podcast from Oliva, the Barcelona-founded startup offering mental health support to businesses, in which top founders and people leaders open up to Maite Otero, a therapist and workplace culture specialist. 

The latest episode features Hannah Francis, Revolut’s head of engagement and executive assistance, and offers a peek into life at the neobank’s notoriously pressurised working environment. Here are three things we learnt:

  • Peers can be valuable first responders for mental health issues. During the pandemic, Revolut introduced a scheme that invited employees to volunteer as “mental health first aiders” who serve as a first port of call for colleagues who are struggling at work. Francis clarifies that this isn’t meant to stand in for professional mental health care, but describes how colleagues with shared experiences — such as new parents working at the company — have offered each other really positive support during these tough times.
  • Wellbeing should be a part of whistleblowing. Whistleblowing in the workplace is about to get a big shake up in Europe, as a new EU directive comes into force that will compel companies with 50 employees or more to implement secure and anonymous channels for raising concerns. Francis notes that Revolut has added a wellbeing section to its new whistleblowing portal, to provide a fully anonymous way for employees to raise issues that might be affecting their mental health.
  • Duvet days don’t always cut it. Francis proudly tells Otero that Revolut has introduced two wellbeing days per year, as a way to tackle employee burnout, but there are flashes of honesty from her own experience that demonstrate that “duvet days” don’t always cut it. Francis concedes that Revolut’s “hugely fast-paced” working environment, combined with her own personal issues, has led friends and family to advise her to start therapy. “I’ve done that avoidance piece,” she admits, before being challenged by Ortero to begin therapy within a month.

Listen to the whole thing here.

Amy Lewin
Deputy Editor

Get in touch with her at
She loves a bit of reader feedback.
Anisah Osman Britton
Founder at 23 Code Street

Get in touch with her at
She loves to hear about the latest in startupland.
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