Head of Sales Enablement

As Head of Sales Enablement, your mission is to equip our sales team with the tools, training, and insights needed to drive consistent, high-impact conversations that convert leads into revenue. You’ll collaborate closely with Marketing, Product, and Revenue teams to build scalable enablement programs that shorten ramp time, increase win rates, and accelerate ARR growth. Your focus is on empowering reps to sell value with confidence and drive urgency to close deals.

Key Responsibilities

1. Onboarding & Ramp

• Design and implement a scalable, structured onboarding program with certification pathways.
• Reduce ramp time by 30–50% through a combination of self-serve content, live training, and shadowing.
• Align onboarding with real-world selling scenarios and create 30/60/90-day enablement tracks.
• Enable new reps to achieve quota within their first full quarter.
  

2. Sales Process Optimization

• Map each stage of the sales process and centralize in Confluence as the source of truth.
• Build stage-specific resources including talk tracks, qualification frameworks (e.g., BANT), and objection-handling tools.
• Shorten average sales cycle time by 20% through improved buyer journey clarity.
  

3. Deal Size & Value Selling

• Train reps in value-based selling with a focus on outcomes over features.
• Introduce ROI tools, enterprise case studies, and multi-year deal strategies.
• Target a 20–30% increase in average deal size (ADS) over 12 months.
  

4. Segment-Specific Enablement

• Develop role- and vertical-specific enablement tracks (AE, SDR, CSM, etc.).
• Tailor sales narratives to construction industry buyer pain points.
• Provide competitive battlecards and segment performance analysis.
  

5. Pipeline & Forecasting Support

• Create stage-based playbooks and content to move deals forward.
• Build opportunity checklists and inspection frameworks to support forecasting and deal reviews.
• Help reps get unstuck and advance pipeline health.
  

6. Ongoing Learning & Training Culture

• Launch monthly micro-trainings, quarterly bootcamps, and certification cycles.
• Build a centralized learning hub using the LMS.
• Incorporate peer-led sessions and top-performer best practices.
• Use assessments to measure and reinforce learning outcomes.
  

7. Sales & Marketing Alignment

• Establish feedback loops between the sales floor and GTM leadership.
• Ensure marketing assets (case studies, sequences, collateral) are adopted and utilized.
• Co-own launch readiness, campaigns, and content alignment.
  

8. Sales Readiness & Analytics

• Track enablement metrics including conversion rates, time to first deal, and training impact.
• Use dashboards to tie initiatives to business results.
• Continuously refine enablement based on performance data and rep feedback.
  
  

9. Product Launch Support

• Lead GTM readiness for product and feature launches.
• Develop internal launch kits: FAQs, messaging, pitch decks, and email templates.
• Partner with product marketing to deliver training and certifications.
  
  

10. Tech Stack Ownership

• Drive adoption of tools including CRM, call recording, LMS, and content systems.
• Streamline and integrate systems to reduce friction and boost rep productivity.
• Regularly evaluate and optimize tech stack to support scale.

Experience

• 5+ years in sales enablement, ideally in a fast-paced startup environment.
• Proven success leading onboarding, coaching programs, and enablement strategy.
  
  

Skills & Expertise

• Strategic thinker with a track record of aligning enablement to business goals.
• Strong business acumen and data literacy; comfortable using KPIs to iterate
• Cross-functional collaborator with experience partnering across Sales, Marketing, Product, and Ops.
• Experienced in adult learning, coaching, and performance-driven training delivery.
• Project manager capable of juggling multiple initiatives and hitting tight deadlines.
  
  

Tools & Platforms

• Familiarity with tools such as Confluence, Hubspot, Gong, Figma, G-Suite, Monday.com, and LMS platforms.
• Ability to design and manage content ecosystems including playbooks, talk tracks, and templates.
  

About You

We want you to be a part of the Clearstory success story so as you engage with us and our team members, it would be helpful for you to understand some of the core characteristics of our team - hopefully, many of these resonate with you!  

• Embody our core values
• Be Curious
• Customer Obsession
• Keep It Simple
• Raise the bar

• Passion and enthusiasm for your work and the Company
• Loves to take the initiative

• An upbeat, positive, and good-to-be-around attitude.
• Sense of humor.
• Is a “doer” with a hands-on approach
• Very high energy.
• Commitment to excellence.
• Operationally focused - thinking about the entire business and not just your role.
• Bright, quick, articulate, able to influence without direct authority, excellent presentation and interpersonal skills, and able to adapt to different outside constituencies.
• Ability to influence peers, operational managers, and executive team.
• People willingly seek out your advice in the planning phase of decisions.
• Strong entrepreneurial nature and approach.
• You foster trust and accessibility.
• Strong prioritization skills.
• Aggressive drive with a can-do attitude.
• Ability to build relationships and earn the respect of other teams.
• Organizational tolerance: able to work with ambiguity and constant change.
• Genuine passion for customer service.
• Enjoys and has implemented change.
• Believes strongly in his/her abilities.

The Company You’ll Join

We are a first-of-its-kind, category-defining software that is revolutionizing the commercial construction industry. Clearstory is digitizing and automating the change order process inside the commercial construction industry. Regardless of what financial software a construction company uses internally, they can use us to share costs with the companies they work with. This is why our integrations team is so critical to our company’s success!

Just as TurboTax did for tax documents and Bill.com did for accounts receivable and accounts payable, Clearstory is doing the same for change order communication between construction companies.

The construction industry is being transformed fast by technology, but the way companies communicate costs hasn’t evolved in decades and still heavily relies on carbon copy paper, spreadsheets, and email to track billions of dollars. These arcane manual processes can take days or weeks and include hours of manual office tasks such as scanning, manually transcribing, and tedious data entry into spreadsheets.

At Clearstory we are changing that and creating a new category  “change order communication,” by intelligently digitizing this age-old process. This leads to an increase in profits, more successful contractor-to-customer relationships, more transparency into a project’s true cost, and less wasted paper! 

We are a Series B 100% SaaS company with impressive credentials for a company at our stage.

The Team You’ll Be Surrounded By

In addition to experienced SaaS sales, marketing, engineering, and product leaders, our team has over 60 years of combined experience in the commercial construction space. At Clearstory we know our customer’s pain points and challenges firsthand and have built a category-defining product that serves the user first.

You’ll be part of an ambitious and collaborative company, committed to growing a supportive and diverse team that is passionate about empowering our contractor customers.

More important than meeting 100% of qualifications, we are looking for collaborative, long-term team members with a growth mindset, a commitment to proactive communication, and a bias towards action, who are aligned and excited with our company’s mission to build the industry standard in digital change order communication for the commercial construction industry.

The Opportunity

As an early member of the team, you will have an exceptional level of impact on the development and iteration of our Company and the workplace culture itself. 

This is your chance to join a team that is bringing game-changing technology to a stagnant, static, pen-and-paper part of the commercial construction industry.

This is an earlier-stage company and as such you will have many intangible benefits that go along with that opportunity such as the ability to influence the culture of your workplace, the ability to make an immediate impact with a product that already has an established product market fit and a healthy and growing user base as well as significant product influence.

Benefits

• Ability to work with a new product category that has already found product market fit
• Hybrid work schedule - this role is 3 days a week in our office here in Walnut Creek and two flex days where you are welcome to come into the office or work from home.
• Executive interaction regularly
• Competitive market-rate salary for a Series A company
• Subsidized healthcare, vision, and dental
• Early equity!

We are an equal opportunity employer and are committed to providing a positive interview experience for every candidate. If accommodations due to a disability or medical condition are needed, connect with us via email at recruiting@Clearstory.com. As a company, we value fairness, collaboration, communication, and leadership and build our teams around these values.