About this role.
Osano is hiring a GTM Enablement Specialist to improve readiness, ramp time, and performance across sales and customer experience teams. The role owns new-hire onboarding, skills workshops, sales playbooks, battle cards, scripts, product collateral, and a centralized enablement-content repository. It partners closely with Sales, CX, Product Marketing, and Product to keep messaging, product knowledge, and customer-facing materials current and consistent. The ideal candidate has 2–4 years of SaaS sales enablement, sales support, sales, or marketing experience and can facilitate engaging virtual and in-person learning. This is a permanently remote U.S. position at a privacy-focused SaaS company.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
3/5Pace & Pressure
4/5Autonomy Level
4/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
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Sample interview questions
I would begin by defining the critical capabilities required at each stage of ramp, such as product knowledge, qualification, discovery, positioning, and objection handling. I would build a blended program using self-paced learning, live workshops, role-plays, call reviews, and manager reinforcement, then certify readiness through observable practice and performance milestones. I would monitor time-to-first-meeting, pipeline creation, early conversion rates, and new-hire feedback to refine the program.
I would set a clear intended behavior and outcome before launch, then track adoption through repository usage, manager feedback, call evidence, and rep surveys. I would compare relevant performance indicators, such as stage conversion, win rates, or cycle time, while accounting for segment and tenure differences. Based on findings, I would simplify, revise, retire, or reinforce the playbook through coaching.
I start with the buyer problem, the business impact, and the specific sales conversation the content must support. I work with product and subject-matter experts to validate accuracy, then distill the material into plain-language messaging, customer examples, discovery questions, differentiators, and objection responses. I test the content with a small group of reps and iterate based on whether it is easy to find, understand, and use in live conversations.
I would map the shared customer journey and identify common moments where consistent messaging is essential, including handoffs, adoption, renewals, and expansion. I would create a governed central repository with shared foundational assets and role-specific guidance where needed. Regular reviews with Sales, CX, Product Marketing, and Product would ensure content has clear ownership, remains current, and reflects feedback from customer-facing teams.
I would describe a situation using performance data, call observations, and manager input to isolate a specific gap rather than assuming a broad training need. I would explain how I created targeted practice, such as a workshop, role-play rubric, coaching guide, and follow-up reinforcement, then measured changes in confidence, behavior, and business outcomes. The key would be demonstrating an iterative approach that connects learning activity to measurable performance improvement.
About Osano
Osano is an innovative B-Corporation built around a simple belief: privacy is a fundamental right. Since day one, we’ve been focused on giving modern enterprises the ability to innovate quickly, stay competitive, and earn customer trust by respecting data privacy and complying with consent guidelines. Our products help organizations operate confidently in a rapidly evolving regulatory and technological landscape.
About the Role
As a GTM Enablement Specialist, you’ll equip our revenues teams with the knowledge, content, tools, and training they need to sell effectively and hit their number faster. You’ll own the delivery of onboarding for new hires, build and maintain our sales and customer experience playbooks and content library, and partner with Product Marketing to keep messaging consistent and current. This is a hands-on, cross-functional role for someone who loves turning complex products into clear, sales-ready enablement. And who measures success by seller readiness and ramp time.
Responsibilities
Sales
- Deliver onboarding and ongoing training – run engaging onboarding and skills-workshop sessions (virtual and in-person) that get new account executives quota-ready and productive as quickly as possible.
- Build the sales playbook – develop and roll out playbooks, battle cards, call scripts, and sales guides that improve seller performance across segments and sales motions.
- Create sales content – produce success stories, case studies, product collateral, presentations, role-plays, and interactive exercises that reps actually use.
- Identify skills gaps – build relationships with reps and sales leaders to surface enablement needs, then tailor content and training to close those gaps.
- Measure and iterate – track content adoption and training effectiveness through participant feedback and performance metrics, and continuously improve delivery.
- Coach and support – provide ongoing coaching to reinforce learning, and help drive a strong learning culture across the sales, CX, and marketing orgs.
Customer Experience
- Support the full customer journey – equip CX with product knowledge, process guides, and talk tracks for renewals, expansions, and common customer questions.
- Build shared, consistent content – create enablement materials that serve both sales and CX, keeping messaging aligned from first touch through renewal.
- Partner with CX leaders – identify skills gaps across customer-facing teams and reinforce learning through coaching and refresher training.
Content Management
- Own the content repository – manage the sales enablement content library, keep it current and easy to find, and train the team on how to use it.
- Keep messaging aligned – partner with Product Marketing and Product to ensure reps always have up-to-date product information and consistent positioning.
About You
- 2–4 years of experience in sales enablement, sales, sales support, or marketing at a SaaS company.
- Exceptional written and verbal communication skills, with the ability to make complex concepts simple.
- A passion for teaching and a solid grasp of adult learning principles; comfortable facilitating engaging sessions both virtually and in person.
- Proven ability to create sales-ready content – playbooks, presentations, guides, and training materials.
- Strong organizational skills and attention to detail, with the ability to manage multiple initiatives at once.
- Ability to work cross-functionally with sales, marketing, product, and leadership.
- A proactive, adaptable mindset. You are comfortable navigating ambiguity and shifting priorities in a fast-paced environment.
- Creative, strategic problem-solving skills.
- Familiarity with learning management systems (LMS), e-learning tools, and sales enablement platforms.
Why Us
- A well-defined career path that’s not just “climbing the ladder” – learn different competencies, skills, and concepts as you progress and get recognized for it.
- Supportive leadership and peers – from sales engineering and product marketing to sales development and demand generation – you’re never in this alone.
- You’ll be stepping into a space that’s on fire – the privacy and regulatory landscape is only growing with a ton of opportunity in front of us.
- You’ll become a privacy expert, including the opportunity to receive your Certified Information Privacy credential.
- You’ll be representing a product that makes prospects say, “This is so awesome” when you demo it.
Benefits
- Competitive compensation + ownership interest for early stake in our success!
- Unlimited paid time off with a requirement to take at least two weeks off per year.
- We’re continuously a Best Place for Working Parents and offer paid parental leave for all new parents + believe that family, however you define it, comes first.
- Osano sponsors individual premiums for base plans at 100% and dependent premiums at 50% for Medical, Dental, and Vision Insurance via Aetna.
- A fully, permanently remote company so you can work from anywhere in the U.S.
- Receive a Macbook + $600 to craft your home workspace
- Annual company trip designed to foster connection, creativity, and having fun together!
- Mental health benefits with free memberships to mindfulness + talk therapy services
A Bit More About Osano
Osano is a leading data privacy platform that helps organizations quickly and confidently comply with laws like GDPR, CCPA, and other global privacy regulations. From consent management to vendor risk monitoring, Osano makes complex privacy tasks refreshingly simple, so companies can focus on what they do best, while we handle the rest.
We’re backed by top-tier investors including Baird Capital, Jump Capital, and LiveOak, and we’re scaling fast with a multi-year runway and ambitious growth plans. We’ve also been recognized as a Great Place to Work for four years running, with 97% of employees saying Osano is a great place to work.
As we grow, we’re looking for individuals who lean into modern technologies and smarter systems to drive efficiency, clarity, and speed; both in our product and in how we operate. If you’re excited by the idea of helping build a high-growth, privacy-first company that embraces thoughtful automation, emerging tech, and intentional collaboration, we’d love to hear from you.
Osano is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, marital status, genetic information, disability, veteran status, or any other characteristic protected by applicable law.
Annual salary information is not provided for this position. Explore salary ranges for similar roles in our Salary Directory ›
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