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5 challenges of hybrid sales – and how to overcome them

Struggling to keep work-from-anywhere teams connected, happy and committed? HubSpot’s Vice President of Small Business Sales, Tara DiCristo-Schmitt, shares tips for tackling friction in remote teams head on.

Two people talk while sitting in front of a laptop in an office.

Hybrid sales teams bring on an exciting competitive advantage: sales cycles are shorter, productivity is up and distributed teams are driving up to 50% more revenue, according to a new report from McKinsey & Company. But the shift to remote work has brought some hard knocks on employees – there’s waning social connectivity, collaboration is less fluid and work-from-anywhere burnout has teams exhausted. 

Here’s the upside: Leaders are getting better at recognising the barriers keeping teams from reaching their full potential and digging into effective solutions. ‘We’re all learning how to do this together’, says HubSpot’s Vice President of Small Business Sales, Tara DiCristo-Schmitt. Check out the best programmes, technology and company shifts enabling high-performing teams to overcome the challenges of hybrid sales today.


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Challenge #1: Building great culture

Creating a sense of community and camaraderie amongst sales teams isn’t just good for morale and Glassdoor reviews – that sense of cohesiveness and shared purpose drives financial performance, too. And while a number of businesses scrambled to assemble ‘culture committees’ – or groups that drive efforts to connect employees with programmes and events – at the onset of the pandemic, DiCristo-Schmitt says accountability is key to their success. ‘What is the intended outcome you want to get from this group over the next three months? How should employees feel as a result of their work?’ she says. 

DiCristo-Schmitt also recommends holding monthly recap meetings where sales teams debrief on how they’re managing – not just as employees, but as humans. ‘You slow down for a minute, and give people a chance to speak about the impact other team members are having on them.’ 

Messaging platforms like Slack can help infuse culture into daily hybrid work life – but only if teams are consistent and intentional about building those strong bonds online. Creating non-work channels for water cooler chatter, setting aside time to highlight wins, and encouraging teams to share funny videos, family photos or their favourite hobbies is a great place to start. ‘We make sure there’s constant communication and energy flowing through Slack’, says DiCristo-Schmitt. ‘Polls and contests can also help create that camaraderie we’re all starving for.’

Challenge #2: Developing talent virtually

Learning the ropes at any new role is tough. Virtual onboarding can feel particularly daunting. ‘Some of us are able to feed off what it was once like and morph into this hybrid environment, but new hires can’t’, says DiCristo-Schmitt. And while virtual workshops, Zoom events and team trainings are helpful (Lessonly coaching software is a favourite among the HubSpot sales team, as well as intelligence platform Gong), research shows that simply making sure new hires are comfortable and set up with their tech is paramount. When interns and entry-level hires can rely on their remote work setups, it becomes 85% easier for them to connect with peers and to reach out for help when needed, according to a study from MIT’s Sloan School of Management.

Pairing new sales hires with a mentor is a great way to get questions answered and kick off the all-important network building (and thanks to remote work, connecting with a broader range of colleagues is easier than ever). Encouraging casual coffee chats over Zoom with colleagues is another way to help new hires jive with the values of an organisation. Adding additional support roles into the mix can help grease the transition for new hires, too. ‘We implemented a new role called a ramp acceleration manager – it’s someone there to fill the gap and be another connection point’, says DiCristo-Schmitt.

Challenge #3: Preventing always-on burnout

The freedom to work from anywhere can make it hard to hang it up for the night – particularly for sales teams grinding to make their quota. Leaders can help set healthy boundaries (i.e. perhaps schedule that midnight Slack for the morning) and encourage unplugged time off. ‘We take an annual week of rest and offer holiday quota relief’, says DiCristo-Schmitt. (In other words, sales reps get anywhere from a 25% to 50% quota reduction the month they take their holiday – so there’s less pressure to take calls from the beach.) Skipping internal meetings or Zoom calls on Fridays is another way to give teams a breather.

Another strategy to lighten up the team’s load is to push for technology that puts information at employees’ fingertips. With HubSpot's sales software, you can track and analyse sales activity in real time. Meanwhile, sales documents and pitch decks can live in an organised, central place like Dropbox

Automating pesky admin tasks that eat up time is another stress-saver. (For example, you can make it instantaneous for leads to sign contracts online with eSignatures in Dropbox, powered by HelloSign.) Making sure all the tools your team works with are integrated can reduce manual errors and time spent jumping from app to app. (Experts call that ‘context switching’ and it’s been proven to stress people out.)

HubSpot’s new integration with HelloSign is an easy way to streamline and organise your eSignature needs – so you can forget about frustrating contract errors, lost docs and time wasted while working in your CRM. Deals get closed faster, and teams regain a sense of control in the face of pressure – something critical to their success and well-being. 

Challenge #4: Collaborating effectively

Adopting the right tech – then setting guidelines and expectations – is key to virtual collaboration, too.  Syncing with internal teams (like sharing sales proposals, leaving comments and questions and tracking deal progress) works best when employees are on the same page about how and when that communication happens. (At Dropbox, teams are expected to pow-wow during core collaboration hours that overlap between time zones and communicate asynchronously outside of those hours to build in heads-down time.) 

Learning how to write crisp, clear emails, create jargon-free strategy docs and deliver concise presentations can help respect your team’s collaboration time and quicken virtual decision making, too. Check out Dropbox’s Virtual First Toolkit for all that and more tips on leading impactful meetings, reducing distractions, and helping your sales team push projects forward in a hybrid or remote setting.

Challenge #5: Gaining visibility

Making a name for yourself and forming relationships with senior stakeholders takes extra effort when you’re working behind a screen, but it’s still critically important. In addition to scheduling virtual lunches with colleagues outside your direct team, take advantage of your company’s Slack or Wiki to share achievements or lessons learned from a recent project, says DiCristo-Schmitt. (Even better – offer to present your findings or insights to your cross-functional peers or at an all-hands meeting.) 

Taking on leadership roles in employee resource groups or volunteering to help with company events and programmes is another way to build relationships outside your direct team – and maybe even meet a few of them in person.