Dovetail is the world’s leading AI-first customer insights hub, on a mission to improve the quality of every thing. We’re redefining what it means to be connected to your customer, giving everyone on the product team fast and easy access to customer insights at any point in the development lifecycle. Founded in 2017, Dovetail’s team is 100+ and growing across our offices in Sydney and San Francisco. We’re seeking ambitious problem solvers from a diverse range of backgrounds, who are desired for their experience, passionate about their craft, and excited about the work we’re undertaking.

As a Customer Enablement Specialist, you will play a key role in delivering high-impact coaching and best practice sessions to customers across the entire lifecycle — from onboarding through to renewal. This role exists to support customer education, accelerate product adoption, and deepen customer engagement at scale. You will work closely with the Customer Success team, Senior Onboarding Manager, Product, and Sales to ensure customers are equipped with the knowledge and strategies to get the most out of Dovetail.

You’ll be joining a growing Customer Success team of 8, spanning Sydney and San Francisco, and contributing to an evolving customer experience function. Your sessions will support both strategic and tactical customer goals, with a focus on driving adoption of our core product.

What you'll do

• Run High-Impact Coaching Sessions. Deliver live and virtual 1:many and 1:1 sessions focused on product education, best practices, and strategic use cases across the customer journey.
• Drive Product Adoption. Support customers in deepening their use of Projects and other Dovetail products, identifying and promoting behavior that leads to long-term success.
• Accelerate New Product Growth. Partner with Product and Growth teams to bring new features to life for customers, designing and running programs that help accelerate adoption and feedback loops.
• Enable Scalable Customer Engagement. Build repeatable playbooks and session templates that can be reused across customer segments to ensure consistent, high-quality experiences.
• Support Cross-Functional Collaboration. Work with Customer Success Managers, Sales, and Solutions Architects to ensure alignment on customer goals and engagement touch points.
• Gather Insights & Influence Roadmaps. Capture recurring questions, feature feedback, and adoption trends during engagements and share insights back with Product and CS leadership.

What you'll bring

• Experience delivering impactful customer education. You’ve led training, coaching, or enablement sessions that drive real value — whether 1:1 or 1:many, live or virtual — and you know how to tailor your approach to different customer needs.
• Strong product and technical intuition. You quickly build a deep understanding of the products you support and can confidently speak to both strategic use cases and tactical how-tos.
• You’re a natural collaborator. You love working cross-functionally with teams like Product, Sales, and CS to deliver a seamless customer experience and share feedback that helps shape roadmaps.
• You care about scale and repeatability. You’re always thinking about how to make things more efficient — whether that’s building templates, automating processes, or creating repeatable playbooks.
• You’re empathetic and engaging. You know how to read the room (even on Zoom) and create learning experiences that make customers feel heard, empowered, and excited to adopt new tools.

At Dovetail, we’re passionate about building and fostering an environment where every team member feels supported and valued. We celebrate individualism, welcoming everyone to show up as their authentic selves every day. It’s no secret that diversity builds the best teams, large or small, so we highly encourage applications from people who identify as part of an under-represented group.

Compensation Range: $120,000-$150,000 base salary. Compensation offered will be determined by factors such as location, level, job-related knowledge, skills, and experience. This role is eligible for incentive compensation, equity and benefits.

Benefits

• Equity for everyone. We put our money where our mouth is. No matter your role, we provide equity for all along with competitive salaries. See your investment grow as Dovetail grows.
• Equal parental leave. We offer an inclusive framework of 20 weeks equal paid leave to support new parents. Every family is unique, so you make the call how you’d like to take care of what matters most.
• Work from Anywhere. Although we’re in-office, you can work from anywhere for up to 4 weeks per year to accommodate life.
• Extra paid days off. Enjoy ad-hoc KitKat days to take a step back and spend it however you like. Hit the beach, spend time with your family, pick up that hobby you’ve been meaning to try, or anything in between!
• Develop and grow. Take a course, attend a lunch and learn, or head to a conference. We love to support you any way we can, so expect Dovetail to be your #1 fan when it comes to achieving your career goals.
• Health is wealth. We’ve got you covered for 100% of the premium plans across medical, dental and vision. We also believe that everyone has the right to mental wellness and support. So every Dovetailer has access to Uprise (Employee Assistance Program) for themselves as well as their families.