Sales Manager

Wynne Systems•Michigan City, IN

14d

About The Position

Wynne Systems is seeking a sales leader to improve the sales team’s performance and lead a global team comprising five Enterprise Account Managers across the United States and United Kingdom, a Sales Assistant, and a Sales Engineer. The team sells rental and asset management software, primarily RentalMan and RentalResult, with a smaller TMS portfolio, to large enterprise customers in the equipment rental and construction sectors. The role focuses on new-logo acquisition, supported by growth within existing customers. It reports to the Director of Marketing and Sales. This is a people-leadership role responsible for hiring, developing, coaching, motivating, and holding the sales team accountable. The Sales Manager will establish and enforce the team’s sales framework, operating cadence, standards, processes, reporting, and forecasting discipline. The position emphasizes value-based selling in complex, long-cycle, multi-stakeholder ERP sales, coaching representatives to quantify business impact and build and defend a compelling value case. The Sales Manager will improve demo preparation, delivery, and follow-up, and use post-demo retrospectives to guide continuous improvement. The role also drives representative-led pipeline generation, partners with Marketing on account-based marketing, ensures disciplined deal progression and Salesforce hygiene, and champions approved AI tools for efficiency and sales insight. The manager may join customer calls, demos, or onsite engagements to coach, unblock, or provide continuity while keeping the sales representative accountable for the opportunity. The position coordinates cross-functional support and leads sales planning and reporting for North America and EMEA.

Responsibilities

Recruit, onboard, train, coach, motivate, and manage Enterprise Account Managers, setting expectations and holding the team accountable for agreed standards, activities, and outcomes.
Run the sales operating cadence, including weekly one-on-ones, deal reviews, pipeline inspection, scorecards, activity reporting, forecasting, and quarterly performance reviews.
Create, document, and operationalize qualification methods, sales-stage definitions, and standard operating procedures for opportunity management, lead follow-up, qualification, demo preparation, and handoff to Contract Management; enforce their use.
Coach representatives to quantify business impact, frame customer pain for C-suite stakeholders, and defend a value case through multi-stakeholder buying processes.
Set and improve demo standards, coach preparation and delivery, and lead post-demo retrospectives; ensure representatives own pain-point framing and value pull-back, with the Sales Engineer acting as a supporting expert.
Coach representatives to generate pipeline through account networks, existing relationships, and territory planning, and hold the team to routine pipeline-generation activity standards.
Partner with the Marketing Manager and senior leadership on target account selection, account-based marketing campaign design, and follow-up execution.
Ensure opportunities progress with clear next steps, owners, timing, and customer follow-up; use Salesforce and AI-assisted tools to identify stalled deals and coach next actions.
Require and maintain Salesforce hygiene across opportunities, accounts, leads, and forecasts.
Promote daily use of approved AI tools to reduce administrative work, improve CRM hygiene, summarize meetings and calls, personalize customer communications, and support pipeline and forecast analysis.
Provide escalation and continuity coverage by joining customer calls, demos, onsite engagements, or deal actions when needed, while leaving the sales representative accountable for the opportunity.
Coordinate Product, Professional Services, Customer Success, Contract Management, Marketing, and Finance to unblock deals and ensure internal requests are well-formed, prioritized, and timed appropriately.
Create and execute sales plans for North America and EMEA; participate in month-end, quarter-end, and year-end reporting; prepare evidence-based monthly and quarterly forecasts; and partner with the Revenue Operations Manager to maintain Salesforce as the source of truth.