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Masai

We are looking for an experienced Senior Manager - Sales Trainer who can build high-performing sales teams through structured, practical training. The trainer will coach sales reps and managers on incentive literacy, communication, negotiation, executive presence, objection handling, discovery, and consultative selling—with a sharp focus on improving conversions, productivity, and consistency.
This role will begin as part-time, focused on high-impact interventions, and can evolve into a full-time position based on requirements, results, and scale.
Key Responsibilities
<ul>
<li>Training Design &amp; Delivery
<ul>
<li>Design and deliver sales training programs across the sales cycle: discovery, pitch, objection handling, negotiation, closing, and follow-ups.</li>
<li>Run role-plays, call simulations, mock negotiations, and feedback sessions to build real-world selling confidence.</li>
<li>Create structured learning journeys for new joiners (onboarding) and tenured reps (advanced skills).</li>
</ul>
</li>
<li>Incentives &amp; Performance Enablement
<ul>
<li>Train teams to clearly understand incentive structures, tiering, targets, and behaviours that drive outcomes.</li>
<li>Partner with sales leadership to reinforce right selling behaviours aligned to incentive plans.</li>
</ul>
</li>
<li>Communication, Negotiation &amp; Presence
<ul>
<li>Coach reps on verbal and written communication, customer conversations, and professional presence.</li>
<li>Strengthen negotiation skills: pricing conversations, value articulation, handling discounts, and commitment closes.</li>
</ul>
</li>
<li>Coaching &amp; Field Enablement
<ul>
<li>Conduct call listening, live coaching, and 1:1 performance coaching for reps and managers.</li>
<li>Work closely with team leads to build coaching routines and improve daily execution.</li>
</ul>
</li>
<li>Measurement &amp; Continuous Improvement
<ul>
<li>Track training effectiveness using metrics like conversion rates, show-up rates, call quality, ramp time, and win/loss insights.</li>
<li>Iterate training based on gaps, new product updates, and market feedback.</li>
</ul>
</li>
<li>Content &amp; Playbooks
<ul>
<li>Create and maintain sales enablement assets: talk tracks, objection banks, negotiation frameworks, follow-up templates, and coaching scorecards.</li>
<li>Standardize best practices to reduce performance variance across the team.</li>
</ul>
</li>
</ul>
Desired Profile / Qualifications
<ul>
<li>10+ years of experience training sales teams (inside sales / B2C / B2B ).</li>
<li>Demonstrated success improving sales outcomes through training and coaching.</li>
<li>Strong command over consultative selling &amp; discovery; communication &amp; executive presence; negotiation &amp; objection handling; coaching frameworks and role-play facilitation; incentive understanding and behavioural reinforcement.</li>
<li>Comfortable working with fast-paced teams and performance targets.</li>
<li>Strong stakeholder management—able to influence sales leaders and earn trust with reps.</li>
</ul>
Good to Have
<ul>
<li>Experience in high-velocity sales environments (education, SaaS, fintech, consumer subscriptions, etc.).</li>
<li>Familiarity with tools like CRM (Salesforce/HubSpot), call recordings, LMS, and reporting dashboards.</li>
<li>Experience coaching sales managers and setting up coaching cadences.</li>
</ul>
What Success Looks Like (Examples)
<ul>
<li>Improved conversion and closing consistency within 30–60 days of training intervention.</li>
<li>Higher quality discovery and objection handling as measured via call audits.</li>
<li>Faster ramp-up time for new joiners.</li>
<li>Clear incentive understanding reflected in daily activity and behaviour.</li>
</ul>