Sales Enablement Lead

Sales Enablement Lead

Your Work Shapes the World at Caterpillar Inc.

When you join Caterpillar, you're joining a global team who cares not just about the work we do – but also about each other. We are the makers, problem solvers, and future world builders who are creating stronger, more sustainable communities. We don't just talk about progress and innovation here – we make it happen, with our customers, where we work and live. Together, we are building a better world, so we can all enjoy living in it.

Job Summary

The Sales Enablement Lead is a strategic role responsible for transforming our sales organization from product‑focused selling to true customer problem‑solving partners. Leveraging the strategy and program design provided by the Sales Enablement Manager the Sales Enablement Lead is responsible to deliver a modern enablement ecosystem that equips our sales teams to deeply understand customer challenges, engage with industry‑specific insight, and position our solutions in the context of meaningful business outcomes. The lead role will guide the evolution from traditional feature‑based training to a dynamic, continuous enablement program driven by scenario‑based learning, industry playbooks, AI‑powered coaching, and microlearning masterclass series. The ideal candidate is a storyteller, strategist, and educator with a passion for empowering sales teams to deliver measurable impact for customers.

What You Will Do

Transform the Sales Skillsets

• Lead the shift from product/application training toward outcome‑focused, customer‑centric sales enablement.
• Equip reps to diagnose customer challenges such as productivity gaps, cost leakage, downtime, compliance, safety, and operational inefficiencies.
• Deliver frameworks that help teams articulate why customers should care and what KPIs or business outcomes are affected.

Deploy Industry & Persona‑Focused Playbooks

• Deploy tailored playbooks for key industries including Quarry, Civil Construction, Agriculture, and Mining Contractors.
• Define industry challenges, with clear persona segmentation and specific KPIs
• Train reps to position product capabilities through the lens of these challenges.

Deploy the Future-State Learning Program

• Execute masterclass micro‑learning series
• Deliver continuous enablement via:
• Scenario‑based microlearning simulations
• Real customer case studies
• AI‑powered sales coaching
• Deal intelligence reviews
• Win‑loss learning loops
• Digital tools and content for in-field discussions

Drive Sales Performance & Capability

• Partner with Sales Leadership to identify skill gaps and high‑value learning opportunities.
• Enable reps to deliver scenario‑driven demos tied to customer KPIs rather than product walkthroughs.
• Ensure enablement aligns with pipeline quality, deal velocity, and customer success outcomes.

What You Will Have

• Proven experience in Sales Enablement, Sales Leadership, Learning & Development, or similar role.
• Demonstrated ability to create customer‑centric enablement experiences.
• Strong understanding of value‑based selling, discovery frameworks, and outcome‑based messaging.
• Exceptional facilitation and communication skills.
• Ability to translate complex information into simple, actionable programs.
• Strong communication skills.
• Above-average commitment and willingness to travel (up to 50% of the time)

Top Candidate Will Also Have

• Experience in heavy equipment, construction, agriculture, mining, or industrial sectors.
• Knowledge of operations, fleet management, or field service workflows.
• Familiarity with AI‑enabled coaching tools, win‑loss analysis, and competency frameworks.
• Program management certifications or instructional design experience
• Completed engineering or business degree.

Additional Information

• This position requires working onsite five days a week.

How We Support You (Employee Benefits)

Our goal at Caterpillar is for you to have a rewarding career. Our teams are critical to the success of our customers who build a better world. Here you earn more than just wage, because we value your performance, we offer a total rewards package that provides day one benefits along with the potential of a variable bonus. Additional benefits include paid annual leave, flexi leave, medical and insurance. (prorated based upon hire date).

Final Details

Caterpillar is not currently hiring individuals for this position who now or in the future require sponsorship for employment visa status; however, as a global company, Caterpillar offers many job opportunities outside of Singapore which can be found through our employment website at www.caterpillar.com/careers.

About Caterpillar

Caterpillar Inc. is the world's leading manufacturer of construction and mining equipment, off-highway diesel and natural gas engines, industrial gas turbines and diesel-electric locomotives. For 100 years, we've been helping customers build a better, more sustainable world and are committed and contributing to a reduced-carbon future. Our innovative products and services, backed by our global dealer network, provide exceptional value that helps customers succeed.