Sales Coaching - Independent Contractor

Job Summary: Crosscap is engaging Selling 2 Steps Ahead as a contracted sales coaching partner for a focused 12-week program. Selling 2 Steps Ahead delivers expert sales training, one-on-one and team coaching, and fractional sales leadership designed to help teams consistently exceed targets through proven strategies and actionable insights. This engagement is structured around the firm’s Coaching Sessions service ($100/hour), providing direct, personalized coaching to members of the Crosscap sales team to sharpen techniques, overcome pipeline challenges, and drive measurable performance improvement. Job Description: Scope of Work The contractor will deliver up to 10 hours per week of sales coaching services, which may include any combination of the following: 1. Individual & Team Coaching Sessions One-on-one coaching sessions with sales team members targeting specific skill gaps and performance objectives Group/team coaching sessions focused on shared pipeline challenges, objection handling, and deal strategy Real-time feedback on live sales calls, recorded call reviews, and deal post-mortems 2. Sales Process & Methodology Assessment and refinement of the current sales process for moving prospects through the sales cycle Development of a discovery framework and cheat sheet to improve needs-identification and pain-point uncovering Guidance on pipeline management, forecast discipline, and opportunity qualification 3. Messaging & Communication Review and improvement of outbound prospecting messaging, email sequences, and call scripts Coaching on value articulation and simplified messaging that highlights Crosscap’s unique differentiation Support with ROI and business case communication for enterprise prospect conversations 4. Training Library Access (Supplemental) Leverage of applicable modules from the Selling 2 Steps Ahead video training library to reinforce coaching themes Provision of example sales assets (templates, frameworks) that can be customized for Crosscap’s use Key Deliverables Weekly coaching session summaries (key takeaways, rep feedback, action items) Mid-engagement progress report (end of Week 6): assessment of rep development, pipeline impact, and recommended adjustments End-of-engagement summary (end of Week 12): overall performance assessment, skill development outcomes, and recommendations for ongoing development At least one customized sales asset or framework delivered during the engagement Contractor Qualifications Selling 2 Steps Ahead brings the following qualifications to this engagement: Demonstrated track record of sales performance improvement across B2B technology and software markets Experience coaching both individual contributors and sales leadership in enterprise sales environments Structured methodology for skills assessment, coaching cadence, and measurable progress tracking Access to a comprehensive sales training library and battle-tested sales assets adaptable to Crosscap’s market Availability to commit to 10 hours per week for the full 12-week term Worker Type: Temporary (Fixed Term) Number of Openings Available: 1 CrossCap launched 15 years ago as a SaaS to create new digital tools for marketing, as it was moving from the analog world of film to the new digital domain. Our digital tools enabled individuals to change the way they worked and opened multiple new avenues to reach customers. The marketing world is now experiencing a new radical change again.There is significantly more data available today than ever. Combine this with a substantial increase in computing power. AI can utilize both the vast quantities of data and power to provide intelligent augmentation for individuals to change the way work is done. We see AI working with individuals rather than replacing them. Today, intelligent augmentation will streamline work and offer many new ways to effectively and efficiently do your job. CrossCap is an equal opportunity employer, we recruit, hire, train, promote and provide all other privileges of employment to qualified people without regard to age, race, color, creed, national origin, gender, gender identity, gender expression, disability, marital status, veteran status, citizenship status, ethnicity, familial status, religion, sexual orientation or any other classification for which discrimination is prohibited. *** CrossCap does not initiate contact with candidates who haven't submitted their resumes via our official channels, such as Indeed and LinkedIn. All legitimate communications from CrossCap will come exclusively from the crosscap.com domain or No Reply E-mail View email address on click.appcast.io. . We do not use MS Teams or phone calls for initial outreach. If you have applied for a position, please ensure all correspondence is conducted through our official CrossCap.com domain or No Reply E-mail View email address on click.appcast.io to avoid fraudulent interactions.