Principal Enablement Advisor

Showpad•Boston, MA

About The Position

Reporting to the VP of Revenue Enablement, the Principal Enablement Advisor will be the primary architect of Showpad’s formal Enablement Advisory (EA) motion. This role is critical in guiding our clients through their enablement maturity journey, leveraging our software and high-level domain consulting to unlock their full potential. You are an enablement expert passionate about consulting customers on enablement strategy, best practices, ROI optimization and customized solutions that align with their unique business needs and objectives. You will own the transition of advisory from a complimentary, episodic value-add into a robust, recurring service stream with the explicit goal of driving services revenue. By establishing Showpad as a strategic partner rather than just a software provider, you will drive higher win rates on enablement-influenced deals and secure the long-term maturity and success of our global customer base. In doing so, you will empower clients to fortify their Enablement strategy and optimize their usage of Showpad to drive their strategy forward, resulting in palpable Enablement impact and real business results.

Requirements

8+ years of experience in senior enablement leadership roles, GTM strategy, or senior enablement consulting, with proven executive presence and extensive customer-facing experience.
Proven track record of building defensible business cases, demonstrating clear ROI, and aligning enablement initiatives directly to Revenue KPIs and CSuite-level priorities.
Performance oriented with a proven track record of driving Enablement initiatives that align to Revenue KPIs.
Ability to translate modern enablement strategy and lived experience into practical frameworks, models and playbooks for Showpad customers to drive meaningful results (eg demonstrate Enablement ROI, aligning to their Executives, build and drive initiatives that drive GTM performance, secure further investment in the function etc).
A strong and well researched point of view on the future of the enablement domain, and an unwavering passion for the profession that you enjoy discussing with large communities.
Experience in a role that has built something from the ground up successfully.
Comfortable with ambiguity as you design scalable solutions and service infrastructure.
Experience managing complex customer project deployments, leveraging CRMs and the broader tech stack to track, measure, and report progress.
Can mobilize GTM teams and create incentive structures to drive services ARR.
Strong cross-functional collaborator capable of partnering across Revenue Effectiveness, GTM, Product Marketing, and Brand to market and package advisory services.
Demonstrated expertise in organizational change management to ensure long-term framework adoption beyond initial deployment.
A strong, well-researched point of view on the future of enablement, backed by an active portfolio of thought leadership and engagement across large industry communities.

Nice To Haves

Time spent in a quota bearing role considered.
Practical experience building GTM AI Strategy, or guiding teams through AI-driven GTM transformation and modern tech stack integration.
Background in scoping, pricing, or pitching fee-based advisory/professional services.

Responsibilities

Build and scale the Enablement Advisory services infrastructure into a scalable model designed to hit FY27 revenue targets.
Drive the evolution of Enablement Advisory Frameworks and assets such as the Showpad Enablement Maturity Model and develop net-new proprietary frameworks, templates, and "plays" that customers use to define their GTM strategy.
Iterate on the EA playbook in partnership with the VP of Revenue Effectiveness and key stakeholders in Professional Services to ensure alignment between sales and professional services delivery.
Tweak the pricing and packaging strategy for this offering as pipeline is built.
Own the enablement of internal GTM teams, up-skilling them on the Enablement domain to ensure the organization can bring the value of these services to market.
Develop strong and value driven relationships with select prospects and customers by offering tailored Enablement Advisory services in the context of their enablement level of maturity, business challenges and objectives.
Identify high-value prospects where advisory can provide the most impact; own the business case assembly and quantified impact analysis for these deals.
Conduct needs assessments for our clients to identify gaps and opportunities in our clients’ Enablement strategy, process, programs and talent.
Consult customers on a variety of Enablement services including but not limited to; building an enablement strategy, ROI optimization, executive alignment change management processes, designing Enablement programs that stick, and content strategy/ governance models.
Establish executive-facing reporting mechanisms and dashboards to demonstrate the palpable ROI of advisory services to both internal and external stakeholders.
Monitor and analyze client progress and performance.
Deliver insights through regularly occurring deal review cadences, pipeline reviews, and forecast calls.
Contribute to market-facing assets (webinars, blogs, white papers) that Revenue Effectiveness produces that establish Showpad as a domain authority and fuel the top-of-funnel pipeline.
Stay abreast of industry trends, insights, and white papers in the Enablement field.
Use subject matter expertise to fuel the bank of Enablement thought leadership that will be launched to the market and customer communities.
Play a critical role in moderating the customer community and facilitate peer to peer interactions.