Director of Customer Success, Strategic at MaestroQA (Remote)

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MaestroQA is looking for a Director of Customer Success, Strategic to build out our Strategic CS function. This includes driving success for our largest and most strategic clients, and building a team as we continue to scale! You’ll be vital in defining how we partner with these large organizations and continue to deliver value. The ideal candidate is excited about taking significant ownership of this function, and has experience working with large enterprises and building a team.

Who we are

Our mission is to help companies across the world improve their customers’ experiences with better customer support. Our product helps Support Managers coach and develop Customer Service reps, helping them elevate their abilities to deliver great customer experiences and provide data-driven reporting. 

We’re growing rapidly to help reshape how some of the world’s fastest-growing and most innovative companies — including Zoom, Etsy, Stitch Fix, Doordash, Lyft, and Shopify — engage with their customers.

MaestroQA is a rapidly growing B2B SaaS startup -- we are 60 employees, recently raised our Series A, growing at 100%+ each year, and just scratching the surface of our potential. Check out what Forbes wrote about us here!

About our culture:

We have 3 values at MaestroQA that we care deeply about instilling in our culture.

The first is hiring people passionate about their craft and nurturing that passion by designing an experience that creates high ownership, responsibility, and opportunities that stretch people’s abilities. We want to provide you with autonomy, flexibility, and clear impact on our customers and team members. We draw inspiration from Netflix’s No Rules Rules.

The second is hiring people that have strong structured thinking abilities and pairing that with a team that helps improve each person’s decision making skills through questions and socratic debate. We care a lot more about understanding people’s decision making processes more than the decision itself and we actively invest in how to create a culture of healthy debates that are inclusive to all personality types. The primary ask is willingness to explain your logic and willingness to ask others to do the same. We draw inspiration from Thinking In Bets and Super Thinking.

The last value is hiring people who care a lot about evolving themselves for the betterment of their individual, team, and company goals. This often shows itself through stories of people who developed new perspectives on topics over the course of their life and examples of changing their minds based on new data, information, quality of thinking, conversations, etc.. We want to feel everyone is not focused on being right but making the right decision. Right now, we are piloting a Positive Intelligence program with 11 people, including our CEO, to understand their Sabaetours and Sages. This is one example of many other ways we encourage this culture and are excited about new ideas to further this. We draw inspiration from Think Again.

What you’ll do:

As the Director of CS, Strategic, you’ll be working with CX leaders at our largest and most Strategic clients to build innovative Quality Assurance programs that formalize the coaching and development process for their teams. Moreover, you'll be working to ensure that customers continue to push the needle and inspire them to have a higher impact on their business Maestro. This will initially be by working with these clients directly, and scaling a team in the short term as we grow. 

Responsibilities include:

  • Be the main point of contact for our Strategic clients and understanding their business goals
  • Recruit, hire, and train new team members
  • Coach and performance-manage a world-class enterprise CS team
  • Redefine and build the Strategic CS playbook
  • Work with our Senior Implementation Manager to ensure an effective onboarding process aligned around the customer business goals
  • Design and delivering high impact QBRs that clarify value and align on forward looking goals and outcomes
  • Becoming a product, CX, and QA expert and advising clients how to achieve goals through Maestro
  • Building a relationship and “champion” framework to ensure breadth of engagement across these large enterprise organization
  • Working with our AM team to ensure renewals

We are looking for someone that has experience working in an autonomous setting, delivering success with Enterprise clients, and can bring that experience to help architect services and support delivery models for our Strategic segment. Successful candidates will be experienced, yet scrappy and self-driven, excited to join a small company and have a big impact.

Why this opportunity is exciting

There are many reasons this role is an exciting opportunity, but there are 3 that really stand out to us:

    1. Building: You’ll be getting in on the ground floor of a high growth start up. So as the first person and leader on the Strategic CS team, a high performer will have the opportunity to redefine success, build the playbook, and build the team. You’ll be reporting to and working closely with our VP of Customer Success to achieve this.
    2. Product Impact: By working with our most strategic clients, you’ll have a material impact on our enterprise Product Roadmap. Your insight into how Maestro can better support and deliver value to enterprises will make you an important Product Advisor as we continue to move upmarket.
  • Cross Functional Leadership - by working with our largest clients, you’ll not only be involved in product innovation, but also collaborating with Sales and Marketing Leadership as we partner with Strategic clients in the pipeline. Additionally, you’ll build a strong relationship with our Co-Founders (CEO & CTO) as Maestro’s eyes and ears to our highest value clients. 
What you should have
  • 8+ years of B2B SaaS Customer Success experience working with multi-hundred thousand dollar (and larger) account sizes
  • 2+ years of experience managing an enterprise CS team
  • Experience buildings a high performing team - including designing interview processes and recruiting A+ candidates
  • Experience with “workflow” based software and 1000+ users within the client organization
  • Strong customer-facing and presentation skills with the ability to establish credibility with VP and C-level executives and
  • Experience delivering high impact Business Reviews that clarify value
  • Experience building champions at Enterprise organizations and multi-threading relationships
  • Superb written and verbal communication skills
  • Experience working closely and building trust with both Product and Engineering teammates
  • Highly organized and excellent multi-tasker
  • Excited by a high growth and fast paced environment, with the ability to take initiative and adapt 
  • Strong critical thinking and problem solving skills
  • Passionate about helping people, active listener, burning curiosity, and self-driven
What we offer

We are based in NYC but increasingly are remote, and offer competitive pay, stock options, benefits including health insurance, unlimited PTO, and 401k.

At Maestro, we truly value the diversity of thought, perspectives and life experiences of our team. We know that the best outcomes stem from bringing together voices with wide ranging identities, embracing a culture of belonging, and that sustaining a workplace where everyone can bring their full selves is a path, not a destination. 

The biggest perk by far is the opportunity to learn by working on the ground floor and getting to actually build the roller coaster versus just riding it.

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Technology we use

  • Engineering
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Our head office is located right in between Union Square and Washington Square - easily accessible from any part of the city with plenty of lunch options!

An Insider's view of MaestroQA

How does your team reward individual success?

Good performances result in opportunities for great performances! When you prove you can do something well you get opportunities to teach others, build new processes & help the company grow. This doesn't mean "Let's heap more work on Ben!" It simply means, you're rewarded with a chance to shape your role around what you want to do the most.


Customer Success Manager, Mid-Market

What does your typical day look like?

Every day at Maestro is different and I love it! I am never bored and am constantly given an opportunity to grow. Any challenge that we face is tackled as a team and the level of collaboration and trust that we have in one another is something unique and special. We work with an amazing set of customers who I feel invested in supporting long term.


Senior Customer Success Manager, Strategic

What does career growth look like on your team?

There's so much opportunity to grow at Maestro. Within Sales, SDRs get promoted to AEs or AMs, where there's lots of upward mobility between segments, including the possibility to sell multi-million dollar deals. We have a strong feedback culture, which fosters fast growth, and those that are self-starters are able to help build + scale our team.


Director of Sales

What is your vision for the company?

our mission is to create a place people learn and are stimulated by their work more than anywhere else. We teach speed as a habit, emphasize structured thinking, and create space for self and team reflection. We embed our values in all parts of the employee experience, from our approach to hiring, management, culture days, and employee autonomy.



How does your team reward individual success?

We love to promote our team members so they know they are valued & their efforts do not go unnoticed. Incentives, perks, accelerators, continuous training, and development are some of the other ways we invest in our employees.


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