5 Fast-Growing San Francisco Companies Balancing Automation With Human Connection

Customer success leaders share about the ups and downs of embracing automation as they rapidly scale their teams.
Written by Olivia Arnold
September 15, 2022Updated: September 15, 2022

When leaders at Truework are deciding whether to automate different types of outreach, they sort their communication into one of two categories.

The first category is reserved for meaningful outreach moments, such as quarterly and monthly business reviews, during which the client will be happiest to receive touch points from the customer success manager with whom they’ve built a trusting relationship.

The second category is designated for simple updates that customers will be just as content to learn through emails or automated messages.

“For automated outreach, we ask ourselves if removing this task from a customer success manager’s plate will allow them more time to deliver on the human touch points that are so crucial to a healthy customer relationship,” said Mitch Ashcroft, director of customer success at Truework. “If the answer is yes, and making the touch point more automated won’t damage the relationship, then we move it over to automation.”

Truework is one of five San Francisco-based companies that are tackling how customer success teams should balance automation with the human touch as their businesses quickly grow. Leaders were eager to share how they applied automated features to streamline internal workflows and maximize customer outreach, without robbing clients of invaluable human-to-human connection and relationship building.

Built In San Francisco connected with the five customer success leaders below to learn more about the ups and downs of embracing automation as they rapidly scaled their teams. 

 

Brooke Quinn
Chief Customer Officer

 

As the customer success team grows at Carrot Fertility, a healthtech company that connects people to fertility care, the department remains open and flexible to change. While the team looks for opportunities to automate some processes to improve the client experience, Chief Customer Officer Brooke Quinn knows that human interactions are irreplaceable when it comes to fostering partnerships. 

 

What are the most important considerations when scaling your customer success team?

What remains paramount, regardless of organizational size and maturity, is the customer and member experience. Recognizing that not every customer’s needs are the same, it’s important to determine the appropriate support model based on customer size, complexity and product offering. 

A customer success team will undoubtedly look different as an organization scales, and it’s important to remain open and flexible to change. 

There are key indicators that should continually be evaluated to ensure optimal performance across the team – customer satisfaction, net promoter score, net revenue retention (renewal and expansion), engagement and customer health, to name a few. Delivering high performance in these areas will ensure proactive management and scaling of the customer success team and an optimal customer and member experience.

Customers want to partner with organizations keenly focused on innovation and automation, but equally want a thought leader that will become an extension of their team.

 

How are you striking the right balance of automation and human touch?

Automation is key to the continual scaling and maturation of a customer success team. It’s important to continually evaluate the manual processes that are required for successful production and continuity in service but may not necessarily provide a visible value add to the customer and member experience. 

One example is the automation of customer reporting. This is a required asset, but through automation, the effort by the customer success team shifts to analysis, opportunity identification and customer alignment versus time spent on the production of the data. 

Customer engagement will never be replaced by automation; there is tremendous value in establishing and fostering a partnership that drives long-term loyalty to both the product and service offered. Customers want to partner with organizations keenly focused on innovation and automation, but equally want a thought leader that will become an extension of their team.

 

What are the main challenges you’ve faced as your customer success team has scaled? 

The challenges certainly change at different stages of growth. For early-stage organizations, a common challenge can be striking a balance between internal operational effectiveness and automation while continuing to promote rapid business growth and customer acquisition. 

Quarterly evaluation of product and service enhancements, impact analysis and effort to implement are critical to ensure there is a continued laser focus on improvement. Our teams partner closely across the organization to evaluate process and product improvements that will bolster growth, quality and, ultimately, the customer and member experience. 

Improvement and operational effectiveness should be a common language spoken across the team. It’s important that the leadership team is aligned on the practice of balancing growth and operational effectiveness; prioritization of this work starts here.

 

 

Clint Kelson
Director of Customer Success

 

CaptivateIQ, a provider of a commission management platform, segments its business to effectively scale the customer success team without incurring disruptions for clients. Director of Customer Success Clint Kelson says the software company employs automation to streamline simple tasks while regularly ensuring one-on-one interactions between team members and clients.

 

What are the most important considerations when scaling your customer success team?

When thinking about scaling our customer success team, it was important to ensure we were segmenting the business appropriately. This will continue to be an evolution as we grow, expand our customer base and explore different industries. Having, at a minimum, a strategy and foundation for this segmentation was key to minimize customer transitions or disruptions during the customer lifecycle. 

As we scale, we need to continue to make it easy for customers to get the help and support that enables them to use our product. We ensure touch points such as emails and in-app notifications are made at important milestones of the customer journey. Those touch points are engaging and conversational for customers.

Our goals are to help the customer feel they’re part of a broader community with the product, and to optimize the ramp-up process enabling new team members to be effective and knowledgeable as quickly as possible.

As we scale, we need to continue to make it easy for customers to get the help and support that enables them to use our product.

 

How are you striking the right balance of automation and human touch?

We’ve built out an approach that allows for customers to have one-on-one interactions with a member from our customer success team, while also utilizing automation to streamline repeatable tasks, follow-ups and important milestones in the customer journey. 

Examples of how we use automation are: net promoter score surveys and automated follow-ups based on scores; renewal emails and scheduling calls; and success cycles for onboarding, escalations, churned customers and new administrators that prompt tasks for customers or customer success managers. Our customer scores are defined using metrics from product usage, webinar invites, reference calls, case study participation, product updates and recurring surveys. These help trigger automated notifications for customer success managers to check-in and take action. 

Our human touch points are focussed on high-value actions such as when negative sentiments are expressed or we make proactive customer advocacy requests. Examples of this are: recurring product value calls (reviewing product updates, betas, feedback, best practices, etc.); business reviews with executive sponsors and key contacts to show the value of our product and track our goals and initiatives; and renewal calls to evaluate business intent or any obstacles. 

 

What are the main challenges you’ve faced as your customer success team has scaled? 

One challenge was changes in customer segmentation over time as our average customer annual recurring revenue grew. We had to shift our model to keep up with our growing customer base while ensuring we have the right amount of bandwidth to appropriately manage these customer relationships.

Another challenge was establishing a centralized tool for managing all customer touch points and escalations and effectively managing communication across different departments within our organization. Having confidence in the data gathered — as well as ensuring that you are capturing the right data to make informed decisions on when to invest in human touch points — is critical to scaling and maximizing impact.

Introduce customer success managers to customers during the onboarding process to establish trust and credibility. Manage the growth customer segment and identify the right number of touch points with this segment to maximize the impact on churn.

Hire the right people; you have to understand your business and what stage you are at. Some people thrive under constant change and growth, while others like consistency. Be mindful of the change in culture as you grow, as teams can become siloed and you need to keep open communication with the teams that you work with frequently. 

 

 

Anthony Grady
Director of Customer Success

 

The customer success team at Paper, a provider of K-12 tutoring services, is focused on meeting the in-person and digital needs of its unique clients — school district superintendents, administrators and teachers. 

In the beginning of the pandemic, Paper’s team utilized digital tools such as Zoom, Gainsight and Calendly to stay connected to its educators. At the edtech company, Director of Customer Success Anthony Grady works to keep the team committed to its mission by organizing biweekly department sync calls, embracing vulnerability and focusing employees on their “why” for joining the organization.

 

What are the most important considerations when scaling your customer success team?

I always keep three areas of focus top of mind for our customer success department. First is maintaining a team culture. This requires leading with transparency, keeping the work we do fun and always keeping an open-door policy that allows customer success managers to express any concerns or ideas that may help our team achieve success. 

Second, take initiative and be vulnerable. This is something I preach to my team on a daily basis. I love seeing our team brainstorm and come up with ideas that may seem out of the blue at first, but with others’ help, it becomes a well-defined process that turns into a playbook. None of this happens without being vulnerable, putting that crazy idea out there regardless of what others may think. To our advantage, we have built a team here at Paper that helps these ideas come to life. 

Third, remember your “why” — why you work here. Are you truly making a difference? These are things I remind my team of because when you’re having a rough day, these are the reasons that you will decide to push through. Keeping your “why” in the back of your head allows you to operate at the highest level.

With our customer base consisting of school district superintendents, administrators and teachers, maintaining the human touch is crucial.

 

How are you striking the right balance of automation and human touch?

Our engagement model was drastically altered by the pandemic, as it was for many other organizations. Previously, we engaged 100 percent in-person with our customers. With our customer base consisting of school district superintendents, administrators and teachers, maintaining the human touch is crucial to ensuring our customers are heard and that our product is utilized effectively throughout the school year. 

Early on in the pandemic, we were able to develop a proper virtual engagement model to ensure our customer needs were met. Our virtual model consists of hosting frequent check-in calls via Zoom with our customers. Customer success managers utilize tools like Gainsight and Calendly, which allow customer success managers to approach their work from a proactive lense rather than reactive. 

These check-in calls allow customer success managers to build meaningful relationships with our customers. If customers have an immediate need, we have materials prepared to send over virtually, and customer success managers are able to hop on a quick Zoom call to iron out any customer concerns. 

Our goal here at Paper is to meet all of our customers’ needs — whether they are virtual or face-to-face.

 

What are the main challenges you’ve faced as your customer success team has scaled? 

The main challenge I have encountered is making sure the entire team is committed to the overall mission of our company and is not working in silos. If you have a small team, it’s much easier to keep everyone on the same page. However, as your team grows, keeping all customer success managers enthusiastic becomes more challenging. 

In order to increase our team’s resilience, I incorporated biweekly sync calls where all newly developed initiatives, playbooks, general departmental updates, wins and challenges are presented. This call is essential to our department’s success as well as to maintaining our team culture. It also ensures that we operate as a cohesive unit when each customer success manager is in the field. 

Aside from our department’s biweekly meetings, each regional team meets weekly to stay on top of any updated processes. I believe it is essential to hold regular meetings as a department to ensure everyone understands that we are one team working toward one common goal.

 

 

Matt Kudla
VP of Growth and Retention

 

Real estate software company Side utilizes automation for internal workflows, such as creating reports and tracking adoption metrics, thereby preserving time for customer success teams to engage in high-impact client conversations. Vice President of Growth and Retention Matt Kudla emphasizes that scaling customer success teams is a major undertaking that cannot be done successfully in silos, as it requires support from the entire organization. 

 

What are the most important considerations when scaling your customer success team?

A great customer success operation is made of high-impact professionals who drive meaningful engagements with customers. To scale customer success, an organization needs to develop repeatable processes and then support those processes with technology to drive efficiency gains.  

Before changing processes or building out new tools, it’s important to make sure the right people are in place, to be clear on what activities create the most value for customers and to prioritize those activities. Communication, input and alignment from the customer success team and the entire company are imperative to getting this right.  

Once the internal teams have been trained on the new processes and technology gets rolled out, substantial changes to the model can become more difficult.  

Communication, input and alignment from the customer success team and the entire company are imperative to getting this right.

 

How are you striking the right balance of automation and human touch?

When developing our plans for scale, one of the primary goals for the customer success organization was to preserve as much time as possible for the high-impact conversations that deepen relationships and drive value for our partners and our community. Those are the touch points we wanted to deliver more of, and automation can’t replace those interactions.

Our model is to prioritize automating the internal workflows that empower and inform our customer success team, such as creating reports, presentations, tracking adoption metrics and flagging data trends that might indicate an account health issue. From there, our people can make informed decisions about prioritizing what needs to be actioned and communicate directly with our partners.

 

What are the main challenges you’ve faced as your customer success team has scaled? 

At Side, we started our journey with a great team that was already providing a lot of value to our partners. Our opportunity was to organize and support our customer success team’s interactions in a thoughtful way that would be more efficient. 

As we looked at our processes, we recognized a need to revisit and rework some in a way that would not only be more efficient for our internal team, but also be more impactful for our partners. That was a large undertaking, and would not have been possible without the full support of the rest of our organization.

Scaling customer success is not done in a silo, and it will take effort from the entire business to make it happen.

 

 

Mitch Ashcroft
Director of Customer Success

 

At Truework, a provider of an identity verification platform, Director of Customer Success Mitch Ashcroft says that “nothing beats tried-and-true human connection.” While embracing automation, the HR tech company carves out opportunities for person-to-person relationship building at quarterly business reviews and during other periodic outreach sessions. 

 

What are the most important considerations when scaling your customer success team?

The number one thing is to have structure and process in place so every customer success manager can flourish in their role. There is a calmness and confidence that comes from knowing exactly what you need to do and how to do it. 

Ensure everyone is equipped to handle key areas — like how to deliver a quarterly business review, what to do with customer data points and how to handle a renewal or upsell with sales. By removing guesswork from the equation, a customer success team really starts to find their groove and bring a ton of value to a business.

It really sets your company apart these days when you have real humans speak with clients. It shows you value their business and want to give them a voice.

 

How are you striking the right balance of automation and human touch?

We are constantly assessing all the touch points we have with our clients and trying to bucket those touch points into two categories: one, will the customer be happy if a real person delivers this touch point or, two, are they cool with it coming from an email or automated service? 

We are very customer centric and pride ourselves on providing the best experience in the industry for our clients. Nothing beats tried and true human connection, so we make sure all key touch points like quarterly business reviews, monthly business reviews and periodic outreach are all done by a customer success manager either in-person, over video conference or on a phone call. It really sets your company apart these days when you have real humans speak with clients. It shows you value their business and want to give them a voice. 

For automated outreach, we ask ourselves if removing this task from a customer success manager’s plate will allow them more time to deliver on the human touch points that are so crucial to a healthy customer relationship. If the answer is yes, and making the touch point more automated won’t damage the relationship, then we move it over to automation.

 

What are the main challenges you’ve faced as your customer success team has scaled? 

There are a few main challenges that I have experienced. The first is hiring great people who can not only excel in the role at your company but fit really well into the customer success team and on cross-functional teams. 

This takes time, and you need to plan for at least 3 to 4 months of interviewing per open headcount. I suggest leveraging all the tools and resources your company provides, as well as leaning on your own network. 

During the interview process, I also suggest involving other leaders in the cross-functional teams you work with to get their approval of a hire. It shows you are a collaborative leader and want to support the teams around you. 

Processes being updated to fit where your company currently stands can also be a challenge. Process involves many parties and requires a lot of buy-in from many folks. It is key to not only have the right processes in place for the current challenges your company faces, but also look ahead to the next quarter, two quarters and even a year from now, and determine where you think the company will be. What will be required of your team if your company grows by 10 times, 20 times, etc.? Ask yourself what could break your team, and find a solution to whatever that is.

 

 

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