The VP of Sales Consulting & Enablement is a senior executive role reporting to the Chief Revenue Officer that combines deep technical pre-sales expertise with strategic sales enablement leadership. This leader is responsible for bridging technical capabilities and business strategy — equipping sales teams with the skills, tools, and content they need to succeed while personally leading Solution Consulting functions that drive revenue and deliver measurable customer value.
This role is critical in B2B SaaS and technology solutions companies, where the ability to translate complex technical capabilities into tangible business outcomes accelerates deal velocity, improves win rates, and elevates the overall sales organization.
Key Responsibilities
Pre-Sales & Solution Consulting Excellence
Oversee the end-to-end pre-sales framework and process — including discovery workshops, technical qualification, solution design, proof-of-concept (POC) development, demonstrations, and value articulation.
Ensure complex technical capabilities are communicated clearly and compellingly to C-level executives and buyers alike.
Serve as a trusted advisor to clients, prospects, and internal stakeholders, building long-term strategic relationships that support pipeline and expansion revenue.
Stay ahead of emerging market trends, evaluate new tools and platforms, and assess risks to guide product positioning and innovation strategy.
Strategic Leadership & Planning
Define and execute a unified Sales Consulting & Enablement strategy aligned with overall company revenue objectives, focusing on accelerating sales productivity, and improving conversion and win rates.
Lead, mentor, and scale a distributed team of Solution Consultants — including hiring, performance management, and fostering a culture of excellence.
Partner closely with Sales, Marketing, Product, Engineering, and Customer Success to ensure cross-functional alignment across all sales stages and go-to-market motions.
Utilize data-driven insights to continuously improve both pre-sales and enablement initiatives, including onboarding, training, content, and process optimizations.
Enablement Program Development
Design, implement, and manage comprehensive sales onboarding programs to decrease ramp time for new hires and accelerate productivity.
Develop ongoing training, certifications, and coaching initiatives to upskill sales reps, managers, and solution consultants — with a focus on messaging, product knowledge, technical depth, and sales skills.
Create, organize, and maintain a sales enablement content library, including pitch decks, solution demos, case studies, playbooks, and competitive analysis materials.
Ensure timely and effective dissemination of product updates, competitive insights, and value propositions to all customer-facing teams.
Performance Measurement & Analytics
Establish and track key performance indicators (KPIs) for both Sales Consulting and Enablement programs, measuring impact on pipeline, win rates, revenue, and sales productivity.
Utilize analytics to provide insights into content usage, training effectiveness, pre-sales engagement, and areas for improvement.
Present data-driven insights and reports to executive leadership, clearly outlining the impact of programs on revenue outcomes.
Cross-Functional Collaboration
Act as a strategic liaison between Sales, Product, Engineering, and Customer Success to ensure alignment on customer needs, product feedback, and go-to-market execution.
Collaborate with Product Marketing to align on messaging, buyer personas, and competitive positioning, ensuring consistency across all sales touchpoints.
Partner with Customer Success to gather client feedback that informs sales training content, solution design, and product strategy.
15+ years of experience in technical Sales Consulting, Pre-Sales, or Sales Enablement in a B2B SaaS or technology solutions environment.
Proven track record of leading and scaling high-performing, geographically distributed pre-sales or enablement teams.
Deep technical knowledge of enterprise software platforms (HCM, ERP, or adjacent) and broader industry trends.
Strong business acumen with the ability to connect technical capabilities to measurable business outcomes.
Exceptional communication and executive presentation skills; ability to influence C-level decision-makers and internal stakeholders.
Experience building and managing enablement programs, including content strategy, onboarding, and sales training.
Data-driven mindset with experience leveraging analytics platforms and CRM tools to measure and improve performance.
Strategic thinker with the ability to operate both at the executive level and in the field when needed.
Ability to travel up to 35% of the time.
Comprehensive medical, dental, vision, and life insurance coverage
401(k) matching program
Be part of a fast-growing company with a strong mission and innovative products
Work in a collaborative, remote-friendly environment that values initiative and creativity
Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities that are required of the employee for this job. Duties, responsibilities, and activities may change at any time with or without notice. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
hh2 is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other characteristic protected by applicable law.
COMPANY
After nearly two decades, hh2 Cloud Services continues to advance cloud-based services for commercial construction companies. hh2 offers point solutions for time entry, punch clock, AP routing & approval, credit card transaction coding, reimbursement coding, routing & approval, human resources, daily logs, service management, data aggregation, and pay stubs. hh2 also provides the most robust iPaaS solution for commercial construction.
INVESTORS
Founded in 1990, Capstreet invests in lower middle market software, tech-enabled services, and industrial business services companies. With over 45 platform investments and over 200 add-on acquisitions since inception, Capstreet's investment strategy is focused on utilizing its Capvalue FrameworkTM to accelerate growth and profitability and create long term sustainable businesses. The majority of Capstreet's investments have been with founder- or entrepreneur-owned businesses.