Updated: Aug 19
Work-from-home has ushered in an avalanche of shifts regarding how we not only go about our work, but how we define it.
As legacy companies such as Apple, or particularly the investment banking community – Goldman Sachs, JP Morgan among others – have recalibrated the degree to which employees can remain untethered from their ornate high-rises and sprawling campuses, it's underscored the emerging opportunities for nascent ventures to reel in talent.
While Fortune 500 companies and heavily client-focused enterprises are battling switching costs and friction when it comes to implementing organization-level remote work policies, it's suddenly placed leaner organizations in the driver's seat as they embark on building out new-age structures.
And few organizations are leaner than start-ups, who's lack of a cemented foundation gives them the upper hand in an increasingly evolving working model.
Start-ups bring more white space when it comes to their product and roadmap, but more critically in how they flesh out their org structure.
Early-stage companies are in a unique position where they can build out remote-first best practices from inception, leading to less tension in workflow or policy pivots down the road.
This leaves start-ups with the most sticky fishing lines when it comes to landing the trout-level talent fleeing the seas of inflexible employers, ostracism, and clunky transitions.
Start-up founders often dream of when their logo will grace the visible signage of City XYZ's latest Class A Office building, but every forward-thinking founder also knows that dreams aren't always black and white. Today's color is found in designing remote, distributed teams that – like the new venture itself – shift with the product and demand requirements of the dynamic landscape.
The good news is that this lends itself well for bootstrapped, pre-revenue, or seed round companies who want to scale-in headcount or avoid the fixed cost of a building lease. That said, remote-first start-ups bring their own array of challenges in effectively engineering an entirely remote structure.
Here are a few hallmarks of not just designing, but actually implementing, a functional start-up team dotted across the country, or even throughout the globe.
Center your organization around one communication application. Your teams will likely be spread across a variety of work tools, but aim to consolidate general communication to one place. This could be Slack, WhatsApp, Workplace, or a new trendy app like "breakroom", which I just made up to demonstrate just how many options are out there.
Emails or phone calls are inevitable in any workflow environment, but it's difficult to archive takeaways or insights, and there's certainly a "magician effect" where communication vanishes amidst a slew of notifications.
As the new saying goes, "That meeting could have been an email and that email could have be a Slack message" – the latter's advantage being archived in one channel, instead of a non-linear maze of "CC's" or "Reply Alls".
The other upshot is that many communication apps have in-house conferencing tools or partner with a provider like Zoom. Zoom is the cream of the crop for all-hands or really any video call, but Slack or Google Meet within your start-up's Google Workspace can do the trick for quicker, small-scale team chats or one-on-ones.
But the bottom line is to try to generate concise communication in one accessible place, where it can be referenced later, which is why one main application is king. Feel free to share that on your #remotetips Slack channel.
Streamline Project Management Tools
From Trello to Monday to Basecamp to Asana, there's no shortage of project management platforms out there. The lesson here is to centralize teams into one system as much as possible. Some platforms function better for certain departments, such as UI/UX on Trello, sales teams on Salesforce, and marketing on Monday. Ultimately, the larger or multi-faceted your organization becomes, the more likely it is that employees will congregate to what application works best for their process needs.
If your start-up requires the use of multiple tools, you can still generate a one-stop shop by leveraging your preferred communication channel as a central hub. Think of this as like a train station that becomes an access point to multiple on-demand tracks.
If using Slack, try to keep a team's discussion in one thread where members can drop in a link to a Trello card or a Monday task, or documents in a cloud-based portal like Google Workspace. While more granular, project discussions may port over to those platforms, the initial access point is always open, tabulated, and distributed across the entire team.
This effectively creates an over-the-top system on the fly.
Schedule Strategy Sessions vs. All-Hour Message Bombing
With start-ups, inspiration can come at any moment. Early-stage companies often don't follow a traditional 9-5 calendar, which not only adversely effects work-life balance but can lead to idea drain, where worthwhile discussions and insights simply flow out of the system.
Once the entrepreneurial mind kicks into overdrive, it’s easy to message bomb communication threads with concepts, links, and ideas, spilling them out like missiles.
That passion should be encouraged by founders, regardless of what level it's coming from, but it's far more efficient for employees to document and clarify their ideas in an accessible manner before fleshing it out with other team members.
Brainstorming may be 24/7, but organizations should set boundaries on when it's appropriate to introduce ideas and spark discussion. For example, coming up with a new potential customer segment you believe your product can serve at 9:30 PM is highly valuable, but even more valuable if you approach it correctly.
Instead of feeling the need to spread these "must-share" ideas right away, calmly write them down in the notes page on your phone or in your go-to concept journal.
Once your ideas have marinated, schedule a time to share them with a fellow team member over a call or strategy session. This way you receive proper feedback and make sure your ideas come across. Record the results of the session into a Google Doc, and share it via a link to all the relevant people, so they not only see it but also have the ability to provide requisite input.
This process ensures your ideas are disseminated, without being lost in a text thread, or worse, being quickly discarded because the moment is chaotic or inconvenient.
Employ the 24 Hour Rule
Start-ups can be emotionally charged. In a physical office setting, you’re more likely to curb frustration as opposed to enter into a face-to-face confrontation. We've all had reactionary moments that we've come to regret later, and this is where physical interaction usually serves as a protective barrier.
When working on a remote team however, communication is constant, and worse, digital communication is far more impersonal in a business setting. Tone can be difficult to decipher, with confusion and misinterpretation common pitfalls of professional messaging.
iCourage is a real thing, when we're emboldened by technology and operate with less inhibitions or grace than we otherwise would. Venting to a team member or manager is just a text-bubble away in a remote environment, and this is why instituting virtual cubicles of restraint is pivotal.
When frustrated at home, do as you would in the office – take a breath and tangibly remove yourself from the situation. Physically walk away from your phone. It can use some alone time, and so can you. Go for a walk outside as fresh air is a legitimate antidote, and once you return, approach the conflict with more stability, or better yet, employ The 24-Hour Rule.
This long-time concept is more relevant than ever in today's business landscape. It calls for taking a 24-hour break in lieu of immediate action. If you still have grievances after 24-hours, then bring them up once you're on more solid footing and have a clarified understanding of what it is you want to address.
Organize In-Person Meet Ups For Distributed Teams
Face-to-face isn’t as vital during the operational phase of a business, but for an early-stage company trying to establish a culture and cultivate ideation, encouraging remote team members to meet up for coffee if they’re in the same region can be beneficial. These can be purpose-oriented or casual get-togethers. Whether it becomes an ad hoc brainstorming session or simply puts a physical face to a pixel-screen, your organization will feel more tangible.
If certain members of your start-up prefer physical communication, then integrate that into your hiring strategy, placing those employees or freelancers within driving distance of each other and relevant team members. Fully remote can and should have some wiggle room, with flexible outings, or optional use of co-working spaces or even distributed micro-offices woven into your infrastructure as you raise funds and your organization scales.
Optionality, customization, and human consideration is key when constructing optimal workflow and enhancing employee satisfaction.
Eliminate Departmental Silos
Start-ups are holistic in nature and the org structure should reflect that. The physical walls of an office wall-off departments as well. While starting your business fully remote, you're at an enviable square one as it pertains to developing an organization sans departmental silos.
When tackling the pain points your venture has set out to solve, it's highly beneficial that everyone from design, engineering, marketing, finance and sales are on the same page. What's resonating in early customer interviews? How does that inform the product? What type of design and requirements are needed? Is the current product being built filling a need that has a marketable path, both in competition and overall market size? If so, what does the pricing look like? How can all of this be pitched to an investor?
This is a smorgasbord of questions, but each no less important than the others. A software engineer can't answer all of these. Neither can an early marketing hire. Nor can a generalist or the founding team – at least not alone.
So often, specialized people or teams in start-ups become so focus-oriented that they make progress in conflict. They build product the target customer doesn't want. They build great product, but the target market is too small to justify the cost. A solid minimal-viable-product (MVP) and market exist, but there's no funding or marketing roadmap to properly launch.
Ultimately, this leads to waste, misinformed assumptions, and asynchronous progress.
The best way to guarantee all facets of your start-up are working in harmony is to promote cross-functional work, and cross-department check-ins. This is like an all-hands meeting, except truly grass root and bottom up.
Encourage early hires to talk to each other across role. Go a step further and provide everyone with even a rudimentary understanding of the entire scope of the business and roadmap.
Create a "Visibility Level" for all team members. As referenced above, document brainstorming sessions and put them in a static place, such as the G-Suite cloud in your Google Workspace, with liberal sharing protocols and comment access. Someone you may not think certain insights are relevant to, very well could be interested in or benefit from them.
This isn't to advocate for forced collaboration or outright requiring all employees to opt-in to a full view of the organization, with the unreasonable expectation that they're able to do their jobs like versatile chameleons. But at minimum, you should at least provide the opportunity for full-organization, on-demand feedback – developing public specs, sheets, and docs in order to facilitate desired, and sometimes necessary, cross-functional behavior.
This process can ultimately be summarized as an "Insight Elevator" at the core of the organization, where both downstream and upstream communication is encouraged, to provide an efficient idea and feedback loop with accessible touch points to every department.
(See Visual Representation at article's end)
Treat Your Employees Like Investors
The gulf between founders and early hires and freelancers should be reduced as much as possible. The lack of a fully formed hierarchy can either be an asset or pitfall of a start-up. Make it an asset by using the lean nature of the roadmap to build lean teams, who can transcend roles. As referenced above, identify people most interested in full-organization visibility and give them a window into a full-spectrum view of the business. The ultimate way to generate buy-in is to make people feel involved.
Treat your team members like venture capitalists – after all, their time is money. Make clear why they should be invested in this particular idea or mission and what their potential reward is. Sell them like you would sell a potential investor.
But put your "stock options" where your mouth is. You can make the value proposition even more tangible to your employees by offering vested ownership in your company. If you're an extremely small upstart and structured as an LLC, consult with a legal advisor, as key employees or freelance service providers can still be offered ownership incentives via "Capital Interest Units."
A surefire avenue to connect your fully remote start-up, both in commitment, dedication, and culture is to work digitally but make employees stakeholders on paper.
Hire Remote Teams In A Lean Way
One reason the equity discussion above is so crucial is because hiring premium talent is going to become even more and more competitive. By building a remote-first company, you can leverage diverse talent pools that penetrate traditional geographic boundaries, even as top-level talent is going to have more optionality themselves.
Offering a work-from-anywhere lifestyle is a major plus in luring today's talent. Adding equity on top is more than just a sweetener. But in the beginning, your start-up may not have the requisite capital to make full-time hires.
Implement a malleable hiring process that lets you scale up or scale down as required, shifting more resources to certain talent at the most efficient and opportune times. While the founding team may be fleshed out, more and more professionals are embracing freelance work. Everything from design, to programming, to marketing, and even sales is available on a marketplace.
Starting with freelancers creates a lean cost-structure and is a good foray into getting your feet wet as an a company employing the services of others. These relationships can be cultivated into full-time arrangements or stay on-demand as needed.
The key takeaway is that as a fully remote start-up, you're not limited to a proximal location and – unlike legacy companies with massive payrolls and office plates – you can mix and match full-time and freelance talent in a more harmonious way, as long as each team member is valued as a legitimate contributor to your venture.
Building out a bespoke team is both exciting but daunting at the same time. Work marketplaces like Upwork are a great tool to post project-based or hourly freelance opportunities or browse off-the-shelf services and tap into a vast remote talent pool. Their platform also can manage independent contractor agreements as well as payment processing.
Huddle.works is an innovative company that provides "pop-up" teams, particularly helpful in producing software for your start-up, along with other branding and strategy services. What makes Huddle unique is that they enable you to pay their sourced creator teams in sweat equity as well as cash, enhancing the relationship between you and the service provider while Huddle handles the legal/payment backend.
We here at BedSideHustle can be a top-level resource for your start-up, helping craft an organizational management blueprint, outfit your team with work-from-home products and accessories from our online store, as well as provide services in business model generation, branding, copywriting, and pitch deck development.
Reach out to email@example.com if you want a "Nightstand Resource" for your Side Hustle or early-stage company.