Technical Coach (Saas, ERP or property tech)

Technical Coach II serves as a senior individual contributor responsible for mentoring and developing Technical Coaches and Customer Support Specialists, ensuring they deliver exceptional technical assistance to customers. This role combines deep technical expertise, coaching excellence, operational performance improvement, and AI-enabled innovation to enhance support effectiveness and customer outcomes. The ideal candidate will have a strong background in software solutions, excellent communication skills, and a passion for fostering growth in others. Technical Coach II acts as a senior subject matter expert for complex products and provides advanced coaching, training, and troubleshooting support to frontline agents while mentoring Technical Coaches through influence and expertise. The role drives technical capability building, escalation reduction, process improvement, and adoption of AI-enabled support solutions. By providing hands-on coaching and creating technical resources, the Technical Coach directly impacts first-call resolution (FCR), escalation rates, and agent confidence.

PRIMARY RESPONSIBILITIES

Technical Support Leadership

• Provide advanced technical coaching to frontline Customer Support agents.
• Conduct 1:1 and group coaching sessions focused on:
• Technical troubleshooting depth
• First Contact Resolution (FCR)
• Average Handle Time (AHT)
• Customer Experience (CX/CSAT)
• Resolution quality
• Mentor and support Technical Coaches to improve coaching effectiveness and knowledge transfer.
• Coach agents handling complex product issues, integrations, accounting errors, and configuration challenges.
• Conduct deep-dive technical reviews and case-based learning sessions.

Complex Product Support Enablement

• Act as a subject matter expert for complex products (e.g., OneSite, Knock, Accounting)
• Drive advanced troubleshooting capability building across teams
• Partner with Tier 2/3, Product, and Engineering to:
• Resolve recurring issues
• Improve knowledge base and documentation
• Lead deep-dive sessions and case reviews for high-complexity scenarios

Technical Enablement Strategy Execution

• Identify skill gaps across agents and Technical Coaches
• Design and implement targeted technical learning paths
• Ensure consistent adoption of best practices and troubleshooting frameworks
• Facilitate advanced technical training sessions

AI, Automation & Innovation
Drive adoption of AI-enabled support capabilities:

• Develop and implement AI-driven solutions (e.g., copilots, automation scripts)
• Perform basic to intermediate coding/scripting (e.g., SQL, Python, automation tools)
• Design and build agentic AI workflows to:
• Automate repetitive troubleshooting steps
• Enhance knowledge retrieval
• Improve agent productivity
• Partner with internal teams to integrate AI into support operations
• Train Technical Coaches and agents on AI tool usage and best practices

Training & Continuous Learning

• Support onboarding, nesting, and upskilling of agents and Technical Coaches
• Ensure product certification coverage across teams
• Develop:
• Microlearning modules
• Quick reference guides
• AI-assisted training materials
• Measure and improve training effectiveness scores

QUALIFICATIONS

Required:

• Bachelor's degree in IT, Business, or related field (or equivalent experience)
• 2+ years in technical support (SaaS, ERP, or property tech preferred)
• Experience supporting complex products (e.g., OneSite, Accounting, CRM tools)
• Minimum 2 years experience as Technical Coach or equivalent role
• Experience in Python, AI tools, automation, or scripting

Preferred

• Certification in Learn2Lead / Lead2Succeed
• Product certifications (multiple modules)
• Coaching Certification
• Proven experience in performance coaching in a metric-driven environment
• 1 year plus in coaching, training, or leadership role

Work Environment

• Fast-paced, customer-focused support environment
• Hybrid work setup
• Occasional overtime or on-call support during critical periods

KNOWLEDGE/SKILLS/ABILITIES

Required – Technical Skills:

• Strong proficiency in platforms (OneSite, Knock, Accounting, etc.)
• Advanced troubleshooting in SaaS environments
• Working knowledge of:
• SQL / data analysis
• Ticketing systems (Salesforce, Zendesk, JIRA)
• Basic to intermediate Python coding/scripting skills
• Experience with AI tools and automation platforms

Coaching & Analytical Skills

• Ability to integrate technical coaching with performance coaching
• Strong data interpretation and KPI management skills
• Skilled in developing actionable improvement plans
• Ability to lead high-impact coaching conversations