Build Your Career and Future at Wynne.

Job Summary:

Wynne Systems is looking for a sales leader to continue the transition of the sales team to world class performance. This is a people-leadership role: you will hire, coach, and hold Enterprise Account Managers accountable, and you will build the sales framework, operating rhythm, and process discipline the team runs on. New logo acquisition is the primary growth objective, supported by expansion within our existing customer base.
Reporting to the Director of Marketing and Sales, you will lead a global team that includes five Enterprise Account Managers across the US and UK, a Sales Assistant, and a Sales Engineer. The team sells Wynne’s rental and asset management software, primarily RentalMan and RentalResult with a smaller TMS portfolio, into large enterprise customers in the equipment rental and construction sectors. This is a long-cycle, C-suite sale decided by quantified business value, so a core part of the job is coaching reps to build, defend, and land a value case rather than a feature pitch.
The demo is the decisive moment in our sales cycle. This role owns making demos measurably better over time: setting the preparation standard, coaching delivery, leading post-demo retrospectives, and feeding what is learned back into how the next one is run. We want someone who treats demo quality as a discipline to be built rather than a talent reps either have or do not.

Job Description:

Objectives of this role

• People leadership first. Hire, train, coach, motivate, and hold the sales team accountable for new logo and existing-customer sales across the United States and United Kingdom.
• Value-based selling. Coach reps to lead with quantified business impact in a complex, multi-stakeholder ERP sale where deals develop over years rather than quarters.
• Sales framework and operating discipline. Build, install, and enforce the sales framework, activity standards, scorecards, deal reviews, forecasting discipline, and structured one-on-ones.
• Demo excellence. Drive preparation, delivery, and follow-up so every demo is exceptional.
• Pipeline generation and marketing partnership. Shift the team toward rep-led pipeline generation and partner with Marketing on ABM strategy and execution.
• Deal progression and communication discipline. Ensure opportunities move forward with clear next steps, owners, timing, CRM updates, and timely customer follow-up.
• Escalation and continuity coverage. Join customer calls, demos, and onsites when needed to coach, unblock, or provide continuity, with the sales representative remaining accountable for the opportunity.
• AI adoption. Champion the use of approved AI tools to improve efficiency, CRM hygiene, forecasting insight, and customer communication quality.

Responsibilities

• Lead and develop the sales team. Recruit, onboard, train, coach, and manage Enterprise Account Managers, setting clear expectations and holding the team accountable to agreed standards, activities, and outcomes.
• Run the sales operating rhythm. Own weekly one-on-ones, deal reviews, pipeline inspection, scorecards, activity reporting, forecasting, and quarterly performance reviews on a consistent, predictable cadence.
• Build and enforce the sales framework. Create, document, and operationalize the qualification methodology, stage definitions, and sales SOPs covering opportunity management, lead follow-up, qualification, demo preparation, and handoff to Contract Management, then hold the team to them.
• Coach value-based selling. Help reps quantify business impact, frame pain to the C-suite, and defend a value case through multi-stakeholder buying processes, reinforcing a respect-first approach and deep customer and domain knowledge.
• Own demo quality. Reinforce the standard that reps own pain-point framing and value pull-back with the Sales Engineer as supporting expert, and lead post-demo retrospectives to capture what to improve.
• Drive rep-led pipeline generation. Coach reps to source their own opportunities through account networks, existing relationships, and territory planning, and hold the team to activity standards that make pipeline generation routine rather than occasional.
• Partner with Marketing on ABM. Work with the Marketing Manager and senior leadership on target account selection, campaign design, and follow-up execution, making sure marketing-triggered engagement is answered with quality, well-timed outreach.
• Drive deal progression. Ensure opportunities have clear next steps, owners, timing, and follow-up, using Salesforce and AI-assisted tooling to surface stuck deals and coach the path forward.
• Maintain CRM discipline. Require Salesforce hygiene across the team, keeping opportunities, accounts, leads, and forecasts current and credible.
• Champion AI adoption. Drive daily use of approved AI tools to reduce administrative work, improve CRM hygiene, summarize meetings and calls, personalize customer communication, and support pipeline and forecast analysis.
• Provide escalation and continuity coverage. Step into customer calls, demos, onsites, or deal actions when needed due to absence, transition, escalation, or business need, without positioning the role as the default deal owner.
• Coordinate cross-functional support. Orchestrate Product, Professional Services, Customer Success, Contract Management, Marketing, and Finance to unblock active deals and ensure internal requests are well-formed, well-prioritized, and well-timed.
• Deliver sales planning and reporting. Create and execute sales plans for North America and EMEA, participate in month-end, quarter-end, and year-end reporting, roll up monthly and quarterly forecasts with evidence, and partner with the Revenue Operations Manager to keep Salesforce the source of truth.

Worker Type:

Regular

Number of Openings Available:

1