Director of Sales

eSkillz

About The Position

About the Role: eSkillz is looking for a Director of Sales to lead our Sales and Account Management teams. The Director of Sales will lead revenue growth for our professional services firm by developing and executing sales strategies, building high-performing teams, and expanding long-term client relationships. This role partners closely with executive leadership, delivery teams, and marketing to drive sustainable, profitable growth. We are looking for a “hands on” leader responsible for not only supporting the team, but also being heavily involved in prospecting, scoping, and closing key accounts.

Requirements

8+ years of Sales/Business Development experience and 5+ years of leadership experience, including managing sales reps in software professional services/consulting industry.
Proven success selling enterprise HCM, Talent & Development, HR Tech, ERP, or SaaS-adjacent services.
Strong process and project management, problem solving, and decision-making capabilities
Deep understanding of sales processes and systems
Strong leadership and coaching skills for sales teams
Salesforce CRM proficiency with a metrics-driven approach
Proven success in selling professional services or solutions to enterprise clients with consistent track record of meeting or exceeding $3M+ quotas
Strong financial acumen: pricing models, margins, utilization, and deal economics
Exhibit the ability to connect effectively with prospects or customers, build relationships, influence multiple layers within an organization, and uncover opportunities with a value-based approach.
Possess excellent organizational and written & verbal communication skills, with an ability to influence others.
Be a self-confident communicator comfortable engaging with C-level contacts and articulating ideas persuasively in emails and other written communications.
Display confidence, poise, maturity, and resilience in interactions with both internal and external audiences.
Have proven experience managing multiple, competing priorities.
Demonstrate the ability to create structure in ambiguous situations, maintain focus, and design effective workflows.
Showcase creativity to think outside the box and self-governance to execute effectively.
Be goal-oriented with the ability to work both independently and within a competitive team environment.
Exhibit collaboration skills and the ability to work in partnership with various eSkillz internal groups.
Be self-motivated, driven, and possess a dynamic personality with a bias for action and ownership mindset.
Advanced proficiency in Microsoft Office products such as Outlook, PowerPoint, Word, OneNote, and Excel.

Nice To Haves

worked with Cornerstone, Docebo, Workday, or 360Learning

Responsibilities

Lead, coach, and scale a team of BDRs, SDRs and Account Managers responsible for outbound prospecting, existing account growth, and inbound lead qualification.
Establish clear KPIs, performance expectations, activity benchmarks, and conversion targets for sales reps.
Design and refine outbound strategies, messaging, and sequencing in partnership with marketing.
Implement structured call coaching, role-playing, and deal-qualification frameworks.
Review outbound pipelines weekly to ensure consistent opportunity creation and quality standards.
Foster a high-energy, accountable culture focused on learning and continuous improvement.
Set clear goals for account growth, renewals, upsells, and cross-selling of professional services.
Support sales team in complex negotiations, renewals, and scope expansion discussions.
Ensure consistent execution of account reviews, QBRs, and client success planning.
Establish standardized BDR and AM playbooks and best practices.
Develop clear career progression paths for sales team members.
Promote a culture of high-performance and accountability.
Develop and execute high-impact sales strategies aligned with company goals and revenue targets.
Manage the full sales cycle from lead generation and qualification through proposal, negotiation, and close.
Build and maintain strong, long-term relationships with key enterprise clients and strategic partners.
Analyze sales data and market trends to refine tactics and improve forecasting accuracy.
Drive continuous process improvements across the sales organization.
Identify new market opportunities and growth areas.
Conduct executive-level engagements and negotiate complex contracts and proposals.
Own revenue forecasting, pipeline management, and attainment of quarterly/annual sales goals for both yourself as an individual contributor and your team.
Provide accurate forecasting, pipeline reporting, and deal reviews to executive leadership.
Collaborate with Executive leadership and Revenue Operations teams to develop, track, and manage sales KPIs and the forecast process; conduct performance analysis to drive business decisions and ensure the sales team achieves their goals.
Partner with marketing, delivery teams, and technical consulting teams for solution alignment.
Contribute to the ideation and execution of eSkillz solution-specific marketing campaigns and events to boost lead volume.
Develop and strengthen strategic alliances with LMS/TMS software partners by educating their sales and customer success teams, enabling them to identify. opportunities within their customer base and ensure eSkillz is top of mind.
Drive co-sell motions, partner-sourced pipeline, and joint account planning with software vendors.
Represent eSkillz in partner meetings, events, and executive briefings.