A Push System for Customer Success

Ari Klein - Proactive Customer Success Workflows

"As we shifted away from firefighting mode and transitioned to more closely resemble an Integrated CSM model, the importance of proactively driving value with our key accounts came into focus."

The last eighteen months at DocSend have allowed us to experiment and standardize different proactive customer touchpoints. I’m proud to be able to say that we’ve renewed and expanded nearly all of our strategic accounts.

And some part of that is due to the “push” system we’ve built that’s codified the individual customer touchpoints based on where our customers are in their lifecycle with DocSend.

As a disclaimer: there’s a lot of advice floating around about customer journeys, customer experience, and customer success.

And a lot of it is useful.

But there’s just as much content that’s too generic to put into action. While broad advice can be great, I always strive for specificity and examples to avoid ending up in the same camp, and that’s why I profiled the Customer Success teams at 5 different companies last year.

I’m hoping that you'll walk away from reading this piece with a couple of new ideas to keep in your back pocket or even implement with your team and customers.

First, a little context:

DocSend is a document management, tracking, and presentation solution purpose-built for modern sales and marketing teams. We align the entire team with a centralized content library that's always up to date. DocSend shows which leads are interested, and what content matters to them. You can also present seamlessly from any device — with no downloads required.

We’re an early stage B2B SaaS company targeting enterprise and mid-market clients. Our best fit customers are those that are working five or six figure deals.

In the Beginning

DocSend is freemium-to-premium, so anybody can sign up and upgrade on their own. Unless they’re interested in DocSend Enterprise, in which case they need to chat with us.

But, even a year and a half ago – when we didn’t have as strong of a sense of our ideal customer profile and the value proposition that resonated most deeply – we were working with large enterprise customers.

So, from the very beginning, we’ve operated in two very distinct modes: (1) high touch or “white glove” Customer Success Management for our strategic accounts, and (2) automated outreach paired with passive monitoring for our long tail of lower value customers.

"In the early days, it was easy to fall into the trap of working out of our inboxes. We were sacrificing the important for the merely urgent."

Because we have so many individuals and small teams using DocSend, there’s a constant stream of feedback, requests, and questions to address. In the early days, it was easy to fall into the trap of working out of our inboxes. Dual wielding fire extinguishers, one in each hand, putting out one small fire after another.

But that meant that we weren’t setting aside time for proactive monitoring, relationship building, and account growth activities that drive value for our strategic customers. In short, we were sacrificing the important for the merely urgent.

As we shifted away from being in firefighting mode and transitioned to more closely resemble an Integrated CSM model (as articulated by David Skok here), the importance of proactively driving value with our key accounts came into focus.

A Push in the Right Direction

In theory, mapping the customer journey and identifying important touchpoints isn’t hard. But in practice, when you’re managing a large – and increasing – portfolio of customers who all joined at different times and are at different stages in their lifecycle, it becomes exceedingly complex to stay proactive without a smart system in place.

Specifically, we built an internal "push system" to nudge us about the important – and not just urgent – activities we should be thinking about with each customer. Each notification/task includes a high-level goal (onboarding, adoption, expansion, engagement, or renewal) and a few example tactics and strategies.

Ultimately, whether the suggested tactic is followed, or new ones are improvised, isn’t the point. It’s that we are reminded to proactively monitor and engage and expand the customers that are most important to the business at key milestones in their lifecycle (relating to timeline, product usage, or compelling events).

Guided by Our Goal

We started with the end in mind.

The first thing we did was automate the creation of renewal opportunities so they would, at the very least, be on our radar. We instituted a “contract end date” field in our CRM that is a mandatory requirement for sales reps to complete before a deal is moved to the “closed-won” stage. The renewal opportunity’s projected close date is the “contract end date” + 1 and automatically drives a set of tasks through the life of the customer’s contract.

Because we don’t want to have the same workflow for a $100,000 customer as we do for a $5,000 customer, we can have a different set of tasks automatically generate based on the size of the deal. And, importantly, we also have a push system that sends reminder notifications to us when it’s time to engage, making the process easy to manage.

Let me break down the contents of one of our Customer Success workflows:

  • Create Renewal Opportunity

    • “Contract end date” and “Assigned CSM” fields are required before closing an opportunity.
    • “Assigned CSM” field is a forcing function to involve Customer Success before deals close.
    • Renewal opportunity is automatically created with a calculated “Close date” based on the original opportunity’s “Contract end date”.

    Initial Team Setup

    • Make sure you’ve been introduced as the main point of contact.
    • Verify the customer’s DocSend team is created and is setup with custom branding and other product related setup tasks are complete.
    • Schedule a kick-off call and any trainings or walkthroughs required.

    Evaluate Initial Usage

    • Evaluate initial adoption for each user on the team.
    • Run report and fill out scorecard that delineates key product usage milestones.
    • For those with low adoption score, follow up individually (email, call, personalized video, or another personal touch).

    Get Introduced to New Teams

    • Work to embed DocSend into the new hire onboarding process.
    • Identify most active users and strongest advocates.
    • Map the organization and adjacent teams.
    • Get warm introductions into relevant groups.

    Express Gratitude

    • Thank them for being a customer (e.g. send a handwritten note, email, swag pack, a personalized video, and don’t ask for anything in return)
    • Be as thoughtful as possible

    4 Month Check

    • Review overall engagement by each user on the team.
    • For those with low engagement score, follow up individually (email, call, personalized video, or another personal touch).
    • Document and share all feedback internally.

    Half Year Business Review

    • Deliver insights into usage, team growth, quotes from users, and business outcomes (based on use case).
    • Gauge interest in customer marketing (e.g. case study participation).

    Best Practices Review

    • Set up a meeting to message recently released features, and upcoming roadmap.
    • Offer training sessions for new users (if account has expanded).
    • Renewal opportunity is automatically created with a calculated “Close date” based on the original opportunity’s “Contract end date”.

    Final Product Engagement Check

    • Evaluate product engagement across the team and understand reasoning behind low engagement or churned users.

    Contract Conversation (t-60 days)

    • Refresh your memory on current contract, and create account renewal plan.
    • Get in touch with decision maker to avoid an “11th hour” upsell/renewal conversation.
    • Identify strategic initiatives, any upsell or expansion (size or duration/commitment) opportunity, and discuss appropriate DocSend plan.
    • Communicate any price changes (e.g. expiring promotional pricing).

    Contract Close

    • Negotiate and fully execute the renewal agreement.

Looking Back

Truth be told, we probably did things ad hoc for longer than I would have liked, but that’s the reality of an early-stage, resource-constrained startup. We didn’t arrive at our current process until nearly a year after our product launch, when a few renewals “snuck up” on us.

"You never want to be surprised or have to backpedal into a renewal conversation."

Even though the most important thing after a launch is to land new customers, my one piece of advice is to set some time aside to look ahead and instrument yourself so you’re not caught off guard when it’s renewal time.

Next Up

With our push system instrumented, and an initial concept for customer touchpoints in place, we’re better positioned to provide a consistent, value-driving customer experience for our customers.

For now, this system is working for us, and parts of it may work for your situation too, but we know we can improve!

It’s really only version one for us, and we plan on adapting based on feedback. But it’s done. And in a lot of cases, done is better than perfect.

If you have any questions or any ideas for how we could improve, tweet me @arielklein.

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