Behind the scenes: the Sales culture at Instawork

This last year has been a wild ride. Now that we've established ourselves in the light industrial vertical and seeing a strong return in our hospitality segment, I'm amazed by what the sales team has been able to accomplish. 

As we plan to TRIPLE the size of the sales team this year, I wanted to share a few ways we operate that have contributed to the team's success and how it aligns to our company values.

Always be Learning

We invest heavily into the training and development of our sales team.  Building great empathy for our prospects while working on techniques to enhance our communication and listening skills are life long competencies you will acquire at Instawork. One of the ways we build that competency is via “Kaizen”, which stands for continued improvement in Japanese.  Our “Sales Kaizen” are 3x-a-week training sessions to work on self-awareness, have better conversations with our prospects, and win more business. While it may be daunting to practice among peers, and requires vulnerability on your part, you also have the chance to coach others in these sessions. Team members love the camaraderie and how it lifts everyone to sell at an elite level.  

Group 408

Caption: It's pretty good when you can smile through a training session. 

Empathy, Trust, and Candor

To be fanatical about self-development means we are willing to discuss hard topics with each other.  Empathy, trust, and candor gives us permission to express how we feel without fear of repercussion or politics.  This can be hard to accept at first but we approach all difficult conversations with positive intent which helps to strengthen the bond of trust with our coworkers.

To build trust with each other (and to have a bit of fun), we run themed competitions to help drive output or new process changes.  Teams are drafted across the sales org and points are earned depending on the output we would like to drive - calls, new meetings created, new meetings held, sales made, and more.  There are great prizes, cash, and pride on the line as teams compete to win.  If a team member is not pulling their weight, their teammates will help to strategize how they can step up to contribute.  

Here’s an example of a game we played back in July with the team including old-timey pics of the Account Executives. Who knew you could go back in time?

Act like an Owner

A career in sales is being a mini-CEO of a book of business. As a growing company, taking shortcuts can cost the business greatly in the long run.  For example, we sometimes say “No” to prospective businesses that are a bad fit for Instawork because they can heavily tax our operations teams if they are in regions we don’t support or outside of our worker scope.

Acting like an owner also has benefits for those on the sales team. When there is a business we want, the company does whatever it takes to help them get signed up and successful.  The CEO, myself, our company board, our company advisors, have all jumped in to help prospect, demo, and win deals for the sales team.  If our network or job titles can help bring new partners over the line, then we use this edge to grow our client base.

Acting like an owner means managing our emotions and owning our results even when bad things can happen to us.  We follow the  E + R = O (EVENT + RESPONSE = OUTCOME) formula, which we picked up on from Jack Canfield’s – The Success Principles.  The outcome we desire is a result of how we respond to the events that happen to us.  The top Account Executives always prepare for their week on Sunday so they can take a bias towards action and start their Monday strong.  Prepping their lists, reviewing their calls, building their cadences for the week is the extra step top performers take so they aren’t doing this when they could be talking to customers.  Acting like an owner means being a steward of your time and the very best reps just seem to get more done because they’re more organized.  It also shows up in other ways such as being vigilant around Salesforce hygiene.  Keeping accounts updated with good notes, updating lead statuses, setting call-back times, and managing tasks well leads to more customer conversations and more deals. We believe that a commitment to excellence in something as simple as data hygiene is an investment into our future success. 

Bias Towards Action

We believe in moving fast. The best reps have explosive responsiveness with their prospects.  Does a partner respond to a prospecting email? Great! Call them to qualify and set a meeting instead of going back and forth over email. In a remote world, it is so much better to build a relationship over the phone or zoom vs. trying to predict how your words can be perceived.  

We are in the people business, which means we do whatever it takes to bring on key prospects assuming it can be done in a safe manner. This includes the willingness to travel to get a deal done.  Given that our prospective Light Industrial partners have been operating throughout the pandemic, having an AE show up in person speaks volumes of our commitment to their success.  After my second shot, I was on a plane visiting our large enterprise customers to grow their accounts. Bias towards action is a bias towards winning.

Values create Enterprise Value

When the pandemic first started, our business ground to a screeching halt.  A hospitality staffing app became irrelevant to universities, stadiums, caterers, country clubs, and event organizers as large group gatherings were banned.  We could have chosen to wait it out or even fold like some of our competitors did. Do you remember, back then everybody believed this pandemic would only last a couple of months?  Instead, we reacted by building out an entirely new division which has become the majority of our growth and success story in 2020 and into 2021.  We took a Bias towards action and reorganized around the light industrial space.  Supply chains were getting disrupted and the need for a flexible labor solution was exacerbated by covid fears and government subsidies.  We Acted like an owner by overhauling our go-to-market faculties.  Lead generation, marketing, website design, personas, sales process, and pricing all had to get overhauled to thrive in the new world.  We made mistakes during the process - lots of them.  Always be learning helped us improve our targeting, managing customer expectations, and growing accounts as we improved our service level agreements.  We found a way to survive and thrive but sometimes when you have to go through a radical change like this, there are going to be a lot of bumps along the way.  Empathy, trust, and candor gave us the tools to help each other manage the emotional toll that a career in sales can bestow upon us and build trust with our peers in a Zoom world.

What I find most compelling about the values of Instawork, is that they drive us to do our best work.  They are the four pillars that give us permission to take bold risks, recover quickly from our mistakes, build trusting relationships with our coworkers, and move fast.  Oftentimes in interviews, a candidate will express their desire to leave their company due to a lack of career progression.  In a high-growth startup, new career opportunities will be seized by those who achieve the results that come with executing against our values. 

Did I mention we’re tripling the sales team? If any of this resonates with you, let’s talk. You can learn more and apply here.

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