Senior Training Executive

Software Finder•201 District, VA

About The Position

We are looking for a Senior Training Executive to own the training function for our cold calling sales team. This is not a generalist training role. We need someone who has lived inside the world of cold outreach and cold calling, ideally in a SaaS or B2B tech sales environment, and knows exactly what separates a rep who books meetings from one who burns through lists. You will own the training function from day one: content, coaching, call reviews, floor sessions, and reporting. You will be expected to bring structure, credibility, and a sharp instinct for where reps break down under pressure.

Requirements

2+ years in sales training with a focus on cold outreach/cold calling.
Direct experience in SaaS, B2B tech, or software sales environments.
Proven track record of improving cold call conversion.
Ability to design training that is practical, not theoretical.
Strong coaching presence: reps should want to be in your sessions.
Familiarity with Aircall or similar dialers.
Experience with CRM environments (HubSpot, Zoho, or similar).
Ability to break down call recordings and give specific, actionable feedback.
Structured reporting and documentation habits.
Comfortable working directly with leadership on performance strategy.

Responsibilities

Design and continuously refine training modules for the cold calling team.
Update reps on product, ICP, and pitch changes as they happen.
Listen to cold outreach calls, live and recorded, document your findings, and deliver focused coaching sessions grounded in what you hear.
Run regular skill-building sessions covering openers, objection handling, tonality, and pattern interruption.
Track rep performance through structured session reports and call observation logs.
Work with the Data Analyst to identify systemic weaknesses and prioritize where to intervene.

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