Growing Self-Serve From 0 To 70%+: The Deputy PLG Strategy For Shift Workers

Readers, I’m excited about today’s newsletter—yes, more so than usual.

It’s about the PLG story of Deputy, an OpenView portfolio company I’ve had the pleasure of working alongside since January 2017. Some fun facts about Deputy:

• Staff management software for businesses with shift workers (think hospitality, retail, cafes, healthcare)
• Founded in Sydney, Australia back in 2008
• Waited more than eight years before raising a Series A, then went on to raise the largest Series B in Australian history
• Hit $100 million AUD in ARR in December 2022

In the past three years, Deputy has seen serious wins in their PLG motion. Self-service conversions have increased from 0 to 70%+ of new customers. Mobile conversion has exploded by 4x. And Deputy’s sales team has had big wins as they’ve been able to focus their time with mid-market accounts like Ace Hardware and Five Guys.

I sat down with Deputy’s PLG dream team—Deepesh Banerji (Chief Product Officer), Dom Newman (Senior Director, Growth and Performance), and Jordan Lewis (Senior Director, Growth)—to go behind the scenes into Deputy’s growth story and lessons learned. Stay tuned for insights on how to build a nurture email program that converts, why mobile is an overlooked acquisition channel in B2B, and why Deputy focuses on the employee to generate referrals and virality.

The scrappy early days: inefficient growth (aka the age of ‘book a demo’)

Prior to 2020, every lead that came in through Deputy’s free trial was routed to a sales rep. This included everyone from mom-and-pop stores with a handful of employees all the way to much larger businesses like Ace Hardware, Everlane, Five Guys, LaserAway, and Trek Bikes.

The approach made sense at the time. Deputy had data that showed free trial sign-ups who hit their “book a demo” call-to-action (CTA) converted at a whopping 55%. Sales reps, meanwhile, demanded more and more leads to hit their quota. Even though very small businesses might require even more time from a rep compared to larger accounts, the team prioritized volume over efficiency—as did many software companies at that time.

It’s no wonder that ‘book a demo’ became Deputy’s main in-product prompt.

“We were falling back on that CTA rather than focusing on getting people to their ‘aha’ moment,” Jordan confessed.

The birth of self-service

Then COVID hit. Like many software companies that targeted the retail and hospitality industries, Deputy’s business took an overnight hit as employees stayed home in quarantine. Main street businesses shut down, stopped hiring, or pivoted their business models.

These external shocks meant that it was time for Deputy to rethink their old way of operating. The growth team decided to run a test. What would happen if they carved out all trial sign-ups for owner-operated small businesses to go through a self-service flow?

Running this test led Deputy to ask all new trial sign-ups how many employees they had. Deputy closely monitored cohort conversion and how it changed over time. Interestingly, conversion rates didn’t budge between before and after the self-service experiment.

Deepesh wasn’t particularly surprised by this outcome.

“Anecdotally, owner-operator small businesses are looking to ‘keep things moving’ and quickly realize value themselves rather than book a time with a sales person,” he reflected.

Since then, Deputy has steadily A/B tested raising the self-serve threshold to a larger and larger cohort of small businesses. As they’ve moved up the threshold, Deputy measured the trade-off in terms of conversion rate, revenue, and efficiency. According to Dom, “There was a slight dip in conversion rate, but the benefits of focusing sales efforts on larger deals well offset any dip that we saw.”

At this point, over 33% of Deputy’s new MRR can be attributed to self-serve. However, for those businesses with hand-raisers looking for more support and guidance, Deputy still offers pathways to join demos, watch on-demand webinars, and walk-throughs with a sales representative. Larger, complex organizations continue to get a white-glove experience with a dedicated sales rep—while at the same time benefiting from a product that hundreds of thousands of businesses can just “pick it up and use.”

The Deputy team attributes their self-service success to mirroring the in-product and email journey to replicate the sales rep’s process. They ensure that there’s a consistent omni-channel onboarding across all surface areas: web, mobile app, email, and education content.

• It starts in the product. Deputy has onboarding surveys, which function similar to how SDRs would’ve previously qualified accounts (company size, industry, and more).
• One-to-many webinars. Deputy replaces the ‘book a demo’ CTA with a one-to-many webinar experience.
• Take the next action. Deputy ditched marketing-heavy emails like “here are three reasons to use Deputy” and replaced them with “take this next product action” themes.

“People like emails that are direct, to the point, and relevant to their product experience. Then we make sure that when people click that email, they land in the product in the exact right place where the email pointed them,” said Dom.

Dom shared an example nurture email sequence for one of Deputy’s popular industry verticals (retail shops) with one popular use case (employee scheduling).

1. Welcome to Deputy. Features a video and emphasizes that folks can get started in just a few steps and whether they’re on the phone or sitting at their desk. The CTA is towards the top of the email. Then Deputy uses remaining real estate to feature specific next steps like setting up your Locations and Areas and reading the getting started FAQs.
2. Your perfect setup. From there, Deputy offers a how-to guide for setting up your first schedule. This email highlights the pain that Deputy solves for scheduling users—replacing inflexible spreadsheets and messy text threads with an app. Everything in the email feels specifically tailored to a retail shop including the imagery, set-up recommendations, and value propositions.
3. Deeper use cases. As a new user completes their first schedule, Deputy introduces deeper functionality including timesheets and exporting to payroll. The payroll email includes a customer testimonial and embeds links to the most popular partners (ADP, Gusto, Quickbooks, and others).
4. Upgrade now. Once new users have started to see value, Deputy pushes for the conversion (upgrade now). These emails highlight one specific plan (Deputy Premium), link directly to Deputy’s checkout screen, and reinforce the value proposition (get ready to have more time in your hands!).

While initially the company identified potential sales risk, Deepesh emphasized that self-service has been transformational to sales efforts as well.

“This has helped us free up sales capacity to go more upmarket with the same size sales team. It’s not either-or, it’s both.”

Turning mobile sign-ups into $$$

As Deputy was nailing self-service conversion on web channels, they started to notice a widening gap between the desktop and mobile experience. The main problem: the mobile app.

In the early days, Deputy’s mobile app was a companion app specifically for end users. It wasn’t a dominant source of new sign-ups and Deputy was OK with lower conversion rates of only 1-2% (these were somewhat higher on iOS and lower on Android).

Deputy decided to make a strategic bet on mobile. After all, when was the last time you saw a cafe or retail business using a laptop computer?

The bet has paid off in a big way. Conversion rates are up roughly five to six times. “The channel that was always there that we never really looked at from an acquisition standpoint finally became a source of revenue,” noted Jordan.

The Deputy team emphasized that the key to their mobile success was taking a first principles approach. They wanted to understand what customers are expecting to get done on mobile, then relentlessly execute with onboarding and solving for jobs-to-be-done to do those things. Here’s a look at how this translated into specific tactics to optimize mobile conversion:

1. Carved out a dedicated product and UX squad who lives and breathes mobile. This squad includes a product manager, product designer, and four to six engineers.
2. Integrated FullStory to see first hand video insights into the app experience. This helped the Growth team spot friction points in the user journey and “tenaciously” optimize for conversion.
3. Rethought their experience in a mobile-first way. This applied to the features that users need to see, the questions they were asked, and the calls to action they saw.
4. Added checklists, gamification, and UX improvements in mobile onboarding. Videos and explainers worked especially well.
5. Introduced in-app purchases, despite the dreaded “Apple Tax.”
6. Clarified how users can combine the best of mobile and web. Mobile can’t do everything for a user–and Deputy doesn’t want it to. They started to provide more context on why users should start on mobile and then go to desktop to complete their experience.
7. Increased discoverability on the App Store. Deputy gets significant organic App Store traffic and has optimized the App Store listing with elegant screenshots, robust app reviews, and winning copy.

Jordan walked me through the winning onboarding flow on mobile from the user’s perspective. Three things to call out as you explore the screenshots below:

• Deputy allows users to sign up in one-click with existing credentials like Apple, Google, or Facebook. This minimizes the need for typing and reduces friction for users.
• Deputy has a three to five question onboarding survey, but emphasizes that the goal of the survey is to “personalise your experience.” Questions include:
  • (a) industry: important for industry-specific communication cadences;
  • (b) team size: used for no touch vs. sales-assist routing;
  • (c) what brings them to Deputy: gauges intent to prioritize trial onboarding features; and
  • (d) how fast they’re looking to get up and running.

• The journey to activation gets highly personalized based on the user’s industry and intent. If the customer selects a cafe/coffee shop, like in the example above, Deputy will pre-populate the most common roles for that specific business. This not only shortens the time to value for new sign-ups, it makes folks feel like Deputy was purpose-built with them in mind.

Winning the employee → winning the business

The Deputy team doesn’t plan to rest on their laurels. They believe that if Deputy can win over the employee, they can win over the business. It doesn’t hurt that employees outnumber managers by 15:1.

Meanwhile, Deputy’s target users—shift workers—tend to either work multiple jobs or change jobs regularly (the average shift worker changes jobs every nine months).

“We see 50,000 people removed from the platform each month and many of them stay in the industry and in jobs that are relevant for Deputy. That’s a massive opportunity for us,” Dom emphasized.

The growth team captures this opportunity through smart outreach and referral programs. Their approach clearly works: over 25% of new sign-ups now come from referrals. Here’s what they do to make it happen:

• Look for a signal. Identify when employees are removed from the platform, indicating they’ve changed jobs.
• Begin outreach. Seven days after an employee is removed, Deputy asks for their new job and for a referral to their new boss.
• Continue outreach. If that doesn’t work, Deputy asks again in one month and then again in three months.
• Incentivize both sides. Folks who refer a new paying customer get a $100 virtual gift card (and so does the business being referred).
• Passion for NPS. Deputy has a passion and focus on net promoter scores (NPS)—or better said, creating a memorable product. NPS is a goal across the entire product development team. With a top tier net promoter score, customers naturally refer Deputy in their day-to-day goings.

Wrap up: Eight learnings from Deputy’s PLG success

• Self-service can help your sales team move upmarket. When sales reps spend more of their time with higher-value prospects, they have a better chance of closing larger deals and hitting quota. Plus, what mid-market customer doesn’t like an easy-to-use, self-service friendly product?
• Test the assumption that sales-assist always outperforms self-service. Deputy started small (less than 10 employee sign-ups), saw success, and then gradually pushed the boundaries of self-service over time.
• Balance growth alongside efficiency and profitability when designing your go-to-market engine.
• Ask questions during onboarding to better understand your users. Deputy’s onboarding survey includes questions about their size (dictates sales outreach), industry, and intent—and they use this data to personalize the onboarding journey.
• Email may not be sexy, but it’s a key part of onboarding and conversion. Deputy personalizes their email nurture cadence based on the user’s industry and intent, mimicking the experience that a sales rep can bring.
• Explore hidden acquisition opportunities on mobile. Deputy managed to 5 to 6x their mobile conversion by taking a first-principles approach to what businesses were looking to accomplish on mobile and relentlessly solving those jobs.
• Winning the employee helps you win the business. PLG companies like Deputy add tangible value with users rather than just managers or buyers. Unlock this opportunity through smart referral offers and well-timed outreach.
• NPS matters. Create a memorable, compelling product and watch the referrals flow in.

Note: Deputy is an OpenView portfolio company. For a full list of OV portfolio companies, visit our Portfolio page.