Hiring Your Startup’s First Customer Success Lead

Customer success (CS) is one of the most critical functions of a startup, especially a business-to-business (B2B) software-as-a-service (SaaS) startup. Your startup’s success depends on educating and keeping customers — exactly what CS professionals are equipped to do. Moreover, when your CS team does its job well, customers turn into advocates, each referring new customers to your business.

If you have the budget, you’ll want to hire someone who has scaled CS at a company similar to yours (in terms of product, sales model, implementation strategy, expansion strategy, etc), from your company’s stage all the way through the initial public offering (IPO). In truth, it’s easier to find a needle in a haystack than to find this mythical ideal hire.

Instead, let’s focus on finding you the best first customer success hire for your startup, starting with the basics.

Generalists: At early-stage startups, you need a jack-of-all-trades who can do whatever is needed, whenever it’s needed. You need someone adaptable and resilient to put out fires while thinking strategically and working proactively. You need someone who can build relationships with customers while also analyzing customer data and trends, turn customer thoughts into focused feedback for the product, scale support, and much more. As your CS department grows, you’ll want folks to specialize: dedicated onboarding specialists, expansion specialists, customer success managers (CSMs) for different customer segments, etc. But at an early-stage startup, hire a generalist.

Coachable, Lifelong Learners: When you work in customer success, you’re constantly learning on your feet. You’ve got to be naturally curious about customers and your product. At an early-stage startup, you must experiment and try different tactics, particularly while working toward finding product-market fit. In addition to hiring for lifelong learners, I recommend hiring for coachability to ensure you hire someone who can grow with your company.

Emotional Intelligence: Every successful CS leader I’ve known exhibits strong emotional intelligence; this is no surprise, given how important it is for CS to have empathy and be able to control their emotions and read customers’ emotions. Since CS often manages angry customers, I also recommend hiring for mindfulness. The ability to stay intentionally focused without passing judgment helps ensure appropriate reactions to defuse charged situations.

Leadership: Your first CS hire won’t be your last. Hire someone who can lead your future CS department — a leader with grace and compassion. Speaking of leading a department, you’ll need your CS lead to have a documentation-first mindset to take what they do, turn it into scaleable processes and teach that to others.

Now that we’ve established the overall traits, let’s go over some factors to keep in mind as you hire your first CS lead.

Product

How complicated is your product? Is specialized knowledge required to understand your product? At Liquid, I’ve found that while no specific expertise is necessary, experience with how businesses contract with freelancers and vendors makes the steep product learning curve much more manageable.

Market

Do your customers speak their own lingo? For example, many of our customers are finance leaders, so it’s beneficial to hire folks knowledgeable about accounting as it pertains to working with contractors and vendors. However, since operations leaders also use our product, finance and bookkeeping expertise are purely optional. Additionally, since many of our customers are agencies or social enterprises, it’d be helpful to hire folks with backgrounds in those industries.

Sales And Pricing Model

Very expensive products with a high-touch sales model will probably require high-touch customer success. “Freemium” products relying on product-led growth, self-service education, and low-touch sales will likely require someone who can more quickly operationalize and scale CS.

Implementation Strategy

How complicated is your product implementation? How quickly do customers see value? Is onboarding straightforward and the same for everyone, or does it vary depending on the specific needs/circumstances of each customer? If it varies, you’ll need someone who asks the right questions to craft customized onboarding/implementation plans for customers. In this case, look for past experience in consulting (or a consultative mindset).

At Liquid, we’ve found that implementation can differ quite a bit between customers depending on a variety of factors — including whether the main users have finance or operations backgrounds, whether they use work orders, how much they care about compliance, whether they are moving from existing tools versus hiring their first freelancer, how many vendors they have, and whether they think of their vendors as a virtual talent bench — but not so much so that custom onboarding plans are needed for each customer. In our case, CS needs to provide high-touch customized onboarding when appropriate, while also operationalizing, scaling, and improving onboarding in general.

Expansion Strategy

What does expansion mean to your company? Is it about selling more licenses? Selling on professional services? Upselling on additional features or higher-level plans? Different expansion strategies require different skill sets. No matter what the expansion strategy, I recommend hiring someone data-savvy enough to segment customers appropriately to identify and pursue potential expansion opportunities.

Company Structure

Who will your first CS hire report to? While I recommend having a customer success lead report to the CEO, I’ve also seen a CS lead report to the chief operating officer (COO), head of sales, and even the chief of staff. No matter how you decide to structure your organization, be intentional about this. Where CS sits in your company says a lot to your employees (and to your customers) about how you view your customers. Choose thoughtfully.

Don’t Delay Hiring Your First Customer Success Lead

As I said at the start, customer success is one of the most important pieces to building a successful company. It’s never too early to hire your first CS lead.

And once your CS lead has created repeatable processes and you’re ready to scale, empower that person to hire a team. I’ve found that non-traditional backgrounds like hospitality, retail, and education lay an excellent foundation of soft skills for CS excellence. If you have the time and resources to train someone (and a product that doesn’t require subject matter expertise), you’re likely to get excellent value hiring folks new to the technology industry.

Are you ready to start building your customer success department?

This article was originally published in Forbes.


Yolanda Lau is an entrepreneurship and small business consultant and a co-founder and partner of Lau Labs. She loves to read. Since 2010, she has been focused on “solving” the “problem” of ambitious, educated, talented women and men “opting out” of the traditional workforce for personal reasons. In 2015, she joined forces with two other MIT alumnae to start FlexTeam — a mission-based micro-consulting firm that matches talented mid-career women with meaningful, challenging, temporally flexible, remote project-based work opportunities. FlexTeam’s clients are businesses of all sizes across all industries and sectors and their most requested projects are market research / analysis, competitor research, financial models / analysis, and business strategy. FlexTeam is also the team behind Liquid.

Five Ways The Pandemic Has Accelerated The Future Of Work

When the COVID-19 pandemic started, few of us had any understanding of how a global pandemic would drastically alter our lives — from curfews and lockdowns to an increase in remote work and an evolving workforce. What we’re seeing is an acceleration of the future of work.

Here’s how the COVID-19 pandemic has and will permanently change how we work.

Soft skills enable adaptability in the future of work.

This year has upended almost everything. It’s become increasingly clear that you can’t just hire for knowledge, content, and hard skills. Hiring adaptable, self-motivated people with soft skills such as mindfulness and emotional intelligence is paying off as these kinds of employees are more adept at adapting to changing circumstances, and learning new skills as necessary.

I’ve found this holds true for employees as well as independent contractors. While some circumstances are well suited for hiring a freelancer to do exactly what he or she has done for another client, I’ve found that looking for soft skills in freelancers results in more successful outcomes, too. This shift has been on the horizon for some time, but the pandemic has accelerated the importance of hiring for soft skills. This should also result in more diverse workplaces, as hiring for soft skills is more equitable across racial, socioeconomic, and gender inequities.

Remote work is here to stay.

With all its benefits and downsides, remote work and telepresence are here to stay. Companies will need to continue to offer remote work as an option to retain top talent, but offices aren’t going away. Working from home has shown us how efficient remote work can be while also highlighting how important face-to-face meetings are for more creative and collaborative work.

What we’ll see post-pandemic is a reexamination of when telepresence is sufficient and when in-person meetings are needed. Companies will choose to reduce office space’s size (and expense), but we’re likely to see most employers land on some hybrid work schedule. Many employees will be able to work from home while being expected to come in from time to time — but executives may be expected to mostly work from the office.

More workers are switching to freelancing; companies are increasingly engaging a global, liquid workforce.

Now that most companies have gone remote, leaders have been forced to focus on outcomes rather than time in the office. This puts freelancers on an ever more equal footing with traditional employees.

Moreover, many of those laid off during this pandemic are choosing to join the gig economy instead of looking for traditional full-time employment during challenging times. People are reevaluating whether employment provides “job security” and more people are concluding that self-employment — with multiple sources of income — may be more secure than a traditional job.

Your company’s workforce of the future will include a greater percentage of 1099 workers. More workers will choose to freelance and work with multiple clients on clearly defined projects — to work only on interesting, challenging projects that suit them. Working in this way allows these freelancers to keep their skills sharper than traditional employees. And so the shift from a blended workforce toward a liquid workforce will accelerate faster.

Also, companies using a liquid workforce can more quickly adjust to changing trends. As executives come to see the advantages of working with a liquid workforce, the gap between companies that activate a liquid workforce and those that choose to rely on a traditional workforce will widen. Agile companies will see greater economic gains and be better positioned for post-pandemic recovery and success.

The expansion of benefits will further accelerate the shift to a liquid workforce.

Moreover, the pandemic has led to freelancers finally gaining eligibility for unemployment benefits due to the CARES Act. With millions left uninsured due to pandemic-induced layoffs, the pressure to disassociate health benefits from the employer-employee relationship has increased. As freelancers’ benefits expand and as health insurance becomes portable, we can expect to see even greater shifts to a liquid workforce.

Software innovation will serve an interconnected workforce.

As work continues to change, so too will the software we use. While the pandemic led to a dramatic increase in video meetings, we are seeing a gradual shift toward a combination of video meetings, memos in lieu of meetings (or as preparation for meetings), and asynchronous video communication via software such as Loom, mmhmm, and Vimeo.

In addition, working remotely has deprived us of serendipitous conversations at the water cooler or break room. Expect to see software innovation to help facilitate these unplanned conversations that often lead to new ideas (and new lines of revenue) — particularly when those conversations are between employees in different teams or departments.

As reliance on freelance workers increases, companies are finding they need software specifically built for contracting, managing, and paying their global liquid workforce. Working with freelancers is very different from hiring employees or managing inventory; companies shouldn’t be managing and paying freelancers via payroll or ERP software. We created Liquid to solve this growing demand.

www.poweredbyliquid.com

We need to prepare for the future.

The pandemic has accelerated the progression of trends that were already underway, including shifting skill sets, more remote work, a growing freelance workforce, and collaboration through innovative software. Now it’s time to prepare for a resilient post-pandemic future. Start by thinking about how the nature of work, work styles, skills, and the workplace have changed over the last year. Focus on the areas that have positively impacted your business and workforce and use this to reevaluate your hiring processes and software solutions. It’s time to embrace a modern business strategy that includes the liquid workforce as an integral part of your talent management. Get ready — the future of work is now.

This article was originally published in Forbes.


Yolanda Lau is an experienced entrepreneurship consultant, advisor, and Forbes Contributor. She is also an educator, speaker, writer, and non-profit fundraiser.

Since 2010, she has been focused on preparing knowledge workers, educators, and students for the future of work.

Learn more about Yolanda here.


FlexTeam  is  a mission-based micro-consulting firm, co-founded by Yolanda Lau in 2015, that matches talented mid-career women with meaningful, challenging, temporally flexible, remote project-based work opportunities. FlexTeam’s clients are businesses of all sizes across all industries and sectors. FlexTeam’s most requested projects are competitor / market research, financial models, and investor decks. FlexTeam is also the team behind Liquid.