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Going 100% Remote: Strategies for Sales and Success


May you live in interesting times. Well, “interesting” is one way to put it. Today’s crisis will touch all aspects of our lives, profoundly impacting human-to-human interactions.

Almost overnight, working and leading remotely went from fringe to mainstream — as did team bonding through virtual lunches and impromptu introductions to kids, partners, and pets. Unfortunately, fear and risk-averse behaviour have become mainstream, too. Though hopefully temporary, these understandable human emotions will have a very real impact on your sales pipelines and your optimal go-to-market strategy.

While there’s no playbook for dealing with the level of uncertainty we’re enduring, we’ll outline some creative strategies to help you survive — and even thrive — while being remote and distributed. With focus, creativity, and flexibility, you and your team can overcome current challenges and emerge even stronger on the other side.

Thriving in a 100% Remote World

Working effectively from home requires a new mindset and approach. Take time to evaluate your personal situation and set some ground rules that will help you — and your family — navigate the workday and reduce friction. If you have kids, make a realistic plan with your partner and your colleagues about how and when you can work. Set up your home workspace to protect sensitive data by using a VPN and enabling Multi-Factor Authentication for all logins (see sidebar on cybersecurity while working remotely). There are many fantastic resources on how to work from home effectively, and here are just a few.

During this transition, it’s more important than ever for management to adjust operating cadence and experiment with creative ways to maintain human connection. Adopt a “Zap, Not Sap” approach to leadership by keeping communications to-the-point and energetic. Consider instituting a daily (or twice-daily) stand up meeting, and experiment with Slack and lightweight employee engagement tools like Officevibe or Qualtrics Remote Work Pulse to stay abreast of morale and dynamics.

Speaking of dynamics, social isolation can easily make us feel anxious and disconnected. Allow time and space for various teams — sales, success, support, sales engineers — to bond by hosting team hangout sessions. Keep these separate from weekly pipeline/forecast calls, and keep it fun — we are all wearing slippers, after all.

Keep in mind that not all questions are best resolved with another Zoom call. In a world where you can’t walk down the hall to ask a question in person, use Salesforce and other analytics tools like Tableau or Looker to stay abreast of your team’s performance and gauge customer dynamics in these unusual times. Learn the metrics that matter and how to find them yourself and review sales cadences as you adapt to a remote workflow. The approach of yesterday should not necessarily become the approach of today.

Mastering the Art of Remote Interaction

As we adjust to a life lived on webcam, best practices for video conferencing are a must. Seth Godin’s nine suggestions for effective video conferencing are a great place to start. While it’s not necessary to set up your room like a professional studio, a little attention to lighting and a good pair of earbuds can make the difference between a seamless call and one interrupted by technical difficulties. It’s always a good idea to test the software before the meeting starts, and — for goodness sake — show up on time. After all, you certainly can’t blame tardiness on the commute!

Video conferencing can be an awkward experience at first, but it doesn’t have to be. Consider starting meetings with an ice breaker to get participants comfortable and engaged. If it’s your job to lead the meeting, decide ahead of time how you will moderate and “call on” participants. Whether you’re talking to colleagues or customers, prioritize human connection overall. We’re living in stressful times, and people are looking to stay engaged.

When communicating with customers and prospects, remember that showing is better than telling. The only thing worse than a PowerPoint presentation is a PowerPoint presentation over Zoom. A short video animation can compress a twenty-minute slideshow into three minutes, leaving more time for meaningful discussion. Modern tools like Vidyard can help you reach past the screen and build authentic connections. Get creative and find new ways to transcend the monotony and deliver “Wow!” moments.

Staying Close to Customers and Cultivating Prospects

Companies that navigate disruptions successfully often do so because they focus on retention and invest in their core customers. Now is the time to call deeper and more frequently into existing accounts. Whereas conventional wisdom encourages relationship-building at the most senior level, the smartest companies will build relationships from top to bottom. Strengthening your long-term relationships will position you well to emerge from this difficult period stronger than ever.

In these volatile times, empathy isn’t just a basic human requirement, it’s a smart business strategy. Support your customers’ changing needs by shifting your orientation toward customer success and sharing best practices. As Gainsight CEO Nick Mehta points out in his excellent post on the importance of customer success, your customers will appreciate a vendor who proactively reaches out with solutions. As customers adapt and seek to reduce the number of partners they rely upon, anticipate needs, ask more questions, and be mindful that preferences are not likely to return to pre-outbreak norms. Remember that your customers, like you, face uncertainty and new challenges. Above all, remember to be human.

For new accounts, the current climate presents unique challenges and opportunities. In the near term, prospects are likely to be risk-averse to spending or shifting incremental budgets. Yet, as we all have more time on our hands, we also seek diversions from the neverending COVID-19 news cycle. We are more open to discovery and education than we were three weeks ago. Now is a great time to cultivate new channels of communication and to educate prospects on the overwhelming benefits of digitally-enabled services and approaches, including an effective content marketing strategy.

Striking the right tone is key. Keep your value proposition front and center, and make it sing in these tough times. Your prospects will be looking for opportunities to do more with less, so adapt your pitch to show them how you can help. Now is certainly not the time for high-pressure tactics. Be mindful of the very real risk of being perceived as opportunistic. Have compassion for the people with whom you’re interacting. Your consideration will be remembered when things go back to “normal.”

Building a Go-To-Market Playbook

As your sales team adapts to remote work, support them by codifying your go-to-market playbook. Every company develops its own process for finding and winning customers: a repeated series of steps on the journey from identifying prospects to closing deals. But like oral history or folklore, this tribal knowledge is rarely written down.

A remote, distributed workplace reveals the key weakness of implicit knowledge: if it’s not written down, you won’t remember it. And you definitely can’t distribute it to new hires. Without a codified go-to-market playbook, new sales reps will struggle to get up to speed, and the rest of the company will be unable to support them.

Take this opportunity to build an explicit go-to-market playbook. Distill your team’s knowledge and articulate your customer journey in clear, simple steps (this YouTube video is a helpful starting point). What do we do and say at each step of the journey? What are the “wows” that excite customers to engage along the way? Lay out this knowledge in a detailed flowchart. Get it down to one page. Then distribute.

Consolidating and documenting your company’s tribal knowledge doesn’t have to stop with the sales team. Learn from effective “all-remote” companies like GitLab, which has compiled thousands of pages of documentation into an easily-searchable handbook that covers relevant topics for every single team in the company. Their “secrets” to a successful remote operation? Be crystal clear and intentional in expectations, and — most importantly — write things down.

This moment is an opportunity to strengthen your company’s processes across the board. Getting everyone on the same page will help your team thrive during this challenging period, and emerge even more connected and powerful on the other side.

Sidebar 1 — Cybersecurity While 100% Remote

While working from home decreases risks to our health, unfortunately it increases the risk of a data breach. Consult with your IT department as soon as possible to determine your game plan for making sure your company’s data is secure.

At the very least, mandatory security and privacy training should be made available, and an IT number or contact email should be distributed. Enable Multi-Factor Authentication (MFA) for all accounts, using hardware tokens (such as YubiKey or Google Titan) if possible. Consider implementing secure tokenization for all personal data, and implement system logging of all actions to monitor for abnormal or suspicious activity.

As work and home life currently take place in the same location, take steps to separate your home and work computer systems. Never copy files to a home computer for printing, or to a personal iPad for reading. Minimize the use of work devices for personal uses such as Netflix or gaming, and never allow family members or roommates to use your work device.

When accessing work systems, always use a Virtual Private Network (VPN), and never use an unsecured WiFi network. If printing is required, use a hard-wired home printer when possible, as networked printers — including printers at Staples and FedEx — could be compromised. Make sure to find a secure storage space for printed documents and printed notes, and invest in a shredder if appropriate.

Sidebar 2 — Capturing Consumers via Content Marketing

In the COVID-19 environment, traditional product discovery and distribution have changed overnight. As brick-and-mortar stores remain shuttered and consumers increasingly turn to online content sources for discovery, reviews, and recommendations, brands can choose from several approaches to reach consumers.

While paid content marketing on Google and Facebook is standard operating practice for all brands, paid marketing via content partnership sites offers another way to reach consumers as they browse for products. Sites like NerdWallet and produce original content and product reviews, and in which you can pay to have your brand listed. Though paid marketing is the fastest way to insert yourself into relevant and accessible content, this ad space is valuable and thus expensive.

Owned content marketing offers brands a way to create content that consumers look to while controlling the narrative and positioning of their product. Brands like Wealthsimple and Policygenius drive traffic by producing topical advice, reviews, and aggregation for the investment and insurance industries, respectively. While it can take months or even years to build a team that can produce relevant, accessible content, organic traffic is substantially cheaper than paid content marketing and can be highly effective in the long run.

Using earned content marketing, brands can create original content to be featured on news sites, blogs, and influencer profiles. The auto insurance pricing index Zebra, for example, produces industry analysis featured in the New York Times. Other common tactics include consumer surveys, original research, or first-to-market innovations. If picked up by a major media outlet, earned content marketing has the potential for wide reach. But it can also be difficult to secure and provide less control over the way your brand is positioned.

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