Director, Premier Account Executive at Omilia

, , Canada -

Full Time

Start Date

Immediate

Expiry Date

06 Oct, 26

Salary

0.0

Posted On

08 Jul, 26

Experience

10 year(s) or above

Remote Job

Yes

Telecommute

Yes

Sponsor Visa

Skills

Sales Leadership, Revenue Growth, MEDDIC/MEDDPICC, Enterprise Sales, Pipeline Management, C-Suite Engagement, Strategic Account Planning, Talent Development, Go-To-Market Strategy, Conversational AI, CRM Proficiency, Commercial Negotiation, Cross-functional Leadership, Forecasting, Account Segmentation, Value-Based Selling

Industry

Software Development

Description

Role Purpose The Director, Premier Account Executives leads and develops a high-performing team of Account Executives responsible for driving net-new revenue and expanding Mid-Market accounts across North America. This role exists to translate Omilia's market vision into tangible pipeline and closed revenue within the premier segment — large enterprises in banking, healthcare, utilities, and insurance seeking to transform their customer experience through conversational AI. The Director is accountable for the team's full-cycle sales performance, talent development, and the disciplined execution of Omilia's go-to-market strategy at the most strategic level of the business. Accountabilities Revenue ownership & target delivery: Own and deliver the North American Premier segment annual recurring revenue target in full, with accountability spanning new logo acquisition, upsell, cross-sell, and renewal performance across the team's entire book of business. Translate the annual target into quarterly and monthly sub-targets per AE, monitor attainment and pipeline coverage on a weekly cadence, and intervene decisively — through reallocation, deal support, or performance management — when trajectory deviates. Provide the NA VP of Premier Sales with a clear, evidence-based view of where the team will land each quarter, never surprises. Team architecture & talent strategy: Accountable for the overall composition, capability, and performance of the Premier AE team. This includes defining the headcount model, leading end-to-end recruitment for open roles, structuring a rigorous onboarding programme that accelerates time-to-productivity, designing a coaching and development framework that raises the floor and ceiling of the entire team, and managing underperformance decisively and fairly. Maintain a healthy internal succession pipeline so that no single departure creates a capability gap. Go-to-market strategy & territory governance: Define, own, and continuously refine the Premier segment go-to-market approach for North America. This includes account segmentation and tiering within Omilia's ICP (Mid-Market companies in banking, healthcare, utilities, and insurance), territory allocation across AEs, prioritisation of verticals and sub-segments by probability and deal size, and alignment of outbound coverage with Marketing's demand generation motion. Review and update the territory model each quarter in response to market data, competitive shifts, and pipeline performance. Executive deal sponsorship & commercial leadership: Act as the senior Omilia executive sponsor on all strategic new logo pursuits, major expansion plays, and at-risk renewals within the Premier segment. Own the relationship with economic buyers and C-suite stakeholders in the most complex and highest-value opportunities. Lead or co-lead commercial negotiations, structure commercial proposals in alignment with Omilia's pricing strategy, facilitate executive business reviews, and personally manage escalations to protect deal health and outcome. Ensure no strategic deal stalls for lack of executive attention. Pipeline health, forecast integrity & sales methodology: Maintain team pipeline at a minimum 5x quota coverage at all stages of the funnel at all times. Enforce rigorous MEDDIC/MEDDPICC qualification discipline across all AEs — no deal advances without documented evidence against each criterion. Own the accuracy of the team's weekly commit, best-case, and pipeline forecasts submitted to the NA VP of Premier Sales. Continuously assess and improve win rates, average deal size, and sales cycle length through structured deal reviews, loss analysis, and methodology coaching. Cross-functional leadership & internal stakeholder management: Serve as the primary liaison between the Premier sales team and all supporting functions — PreSales, Customer Success, Marketing, Product, Legal, and Finance. Ensure that major opportunities are resourced appropriately and that internal stakeholders are aligned on priorities, timelines, and customer commitments. Drive a culture of mutual accountability across functions: PreSales delivers differentiated demonstrations, Customer Success prepares for handoffs proactively, and Marketing generates pipeline in the right accounts. Represent the field's voice in product roadmap, pricing, and packaging discussions. Customer & market intelligence: Maintain deep, current knowledge of the North American enterprise CX and contact centre market — including buyer dynamics, budget cycles, regulatory drivers, and digital transformation priorities in Omilia's target verticals. Monitor the competitive landscape continuously (Nuance, Genesys, NICE, Google CCAI, Amazon Connect, and emerging players) and ensure the team is equipped with current, accurate, and compelling competitive positioning. Feed structured market and competitive intelligence back to Product, Marketing, and the NA VP of Premier Sales on a regular basis to inform roadmap and GTM decisions. Commercial integrity & deal governance: Accountable for the commercial and contractual quality of every deal closed by the Premier team. Ensure all opportunities are priced within Omilia's approved commercial framework, that discounting decisions are escalated appropriately, and that deal structures are sustainable and set up for long-term customer success. Review and approve non-standard commercial terms before submission. Work closely with Legal and Finance on contract governance for complex or high-value transactions. Organisational culture, values & employer brand: Model and actively reinforce Omilia's values — delivering real results, building trust through honesty, innovating through curiosity, pursuing excellence as a habit, and tackling tough challenges — within the Premier team and across the broader sales organisation. Accountable for creating a high-performance, inclusive, and psychologically safe team environment that attracts exceptional talent, retains top performers, and earns Omilia a reputation as a destination for the best enterprise sales professionals in the CX technology market. Key Responsibilities Conduct structured weekly 1:1s with each Premier AE — not status reporting sessions, but working sessions focused on deal strategy, stakeholder mapping, objection handling, and individual skill development. Use a consistent qualification and coaching framework in every session. Document agreed next steps and hold AEs accountable to them the following week. Facilitate weekly team pipeline reviews and bi-weekly forecast calls using MEDDIC/MEDDPICC as the shared language for deal qualification. Challenge every deal classification with evidence-based questions. Identify deals at risk of slipping or losing and co-develop recovery strategies with the relevant AE. Maintain a rolling 90-day view of commit and pipeline at all times. Own the full-cycle hiring process for Premier AE roles — from drafting role profiles and sourcing strategies through to structured interviews, competency assessments, reference checks, and offer negotiation. Define the evaluation criteria in advance of every search, involve PreSales and CS stakeholders in final round interviews, and make hiring decisions grounded in evidence, not intuition. Partner with HR to maintain a warm candidate pipeline and reduce time-to-fill. Design, own, and continuously improve the Premier AE onboarding programme. Ensure every new hire completes a structured 30-60-90 day plan that covers Omilia's platform (OCP, miniApps, Diamant, Pathfinder, CoPilot, Agentic Self-Learning), target verticals and buyer personas, sales methodology, competitive positioning, and internal processes. Track ramp-to-productivity against defined milestones and intervene with additional coaching or resource support if a hire falls behind trajectory. Maintain individual development plans for every AE on the team — covering quota performance, pipeline management discipline, skill development areas, and career progression goals. Conduct formal quarterly performance reviews with documented feedback. Where performance is below standard, initiate a structured improvement plan promptly, with clear milestones, timelines, and consequences. Recognise and reward strong performance visibly and consistently. Engage personally at C-suite and VP level in top-priority opportunities — facilitating executive briefings, presenting Omilia's strategic value proposition and ROI case, participating in proof-of-concept governance reviews, and co-leading commercial negotiations with procurement and legal counterparts. Ensure that Omilia's senior presence in a deal is deployed strategically at moments of maximum leverage, not reactively when a deal is already at risk. Develop and manage a set of named strategic target accounts at the Director level — Mid-Market Companies where Omilia has a strong right to win but where the relationship requires senior-level cultivation over 6-12months. Maintain active relationships with relevant C-suite and senior IT/CX buyers at these accounts, independent of active deal cycles. Collaborate with Marketing to translate segment strategy into specific demand generation activities: targeted ABM campaigns, executive event participation, digital outreach sequences, and content aligned to key buyer pain points. Review campaign performance monthly, provide feedback on lead quality and ICP fit, and co-prioritise the target account list for the next quarter. Work closely with PreSales and Solutions Consulting at every stage of the sales cycle to ensure solution design, demonstrations, and business case development are tightly aligned to the prospect's specific environment, success metrics, and strategic objectives. Debrief after every major loss with PreSales to identify and address patterns in positioning or technical gaps. Own the post-sale transition process for every Premier account. Conduct a formal, documented handoff meeting with Customer Success within 14 days of contract signature. Define expansion triggers, key stakeholder relationships, and risk flags before handoff. Remain involved in executive sponsor capacity for the first 6 months post-close and participate in annual executive business reviews for high-value accounts. Deliver a written weekly forecast report to the NA VP of Premier Sales covering: current quarter commit, upside/best-case, total pipeline, key deal status updates, deal risks, and any required executive support. Maintain a running win/loss log updated after every closed deal. Present a formal quarterly win/loss and pipeline quality analysis with actionable recommendations. Monitor and report on team performance against a defined set of leading and lagging indicators: pipeline coverage ratio, average deal size, average sales cycle length, win rate by vertical and deal size, quota attainment by AE, and forecast accuracy. Use this data to identify coaching priorities, process gaps, and go-to-market adjustments on a monthly basis. Track the competitive landscape on an ongoing basis — maintain current awareness of product developments, pricing changes, win/loss patterns, and GTM moves from Nuance, Genesys, NICE, Google CCAI, Amazon Connect, and other key competitors. Ensure battle cards and competitive objection guides are accurate and in active use by the team. Feed competitive intelligence to Product and Marketing with a structured, regular cadence. Represent the Premier sales organisation in internal leadership forums — QBRs, product roadmap sessions, pricing reviews, and GTM planning cycles. Bring a structured, data-informed perspective to these discussions: what is the market asking for, where is Omilia winning and losing, what needs to change. Act as a constructive, influential voice for the field in shaping Omilia's product and commercial strategy. Knowledge, Skills & Experience Required: Preferably 2+ years of B2B sales experience Proven track record of consistently achieving or exceeding revenue targets in a complex, multi-stakeholder SaaS or technology sales environment. Experience selling into companies(up to 5,000 employees) in regulated verticals s uch as banking, insurance, healthcare, or utilities. Deep understanding of enterprise CX technology, contact centre operations, or CCaaS/CPaaS markets. Demonstrated ability to coach AEs through consultative, value-based, and MEDDIC/MEDDPICC-style sales methodologies. Strong executive presence and the ability to engage credibly with C-suite and VP-level buyers. Proficiency with CRM platforms (Salesforce) and strong forecast management discipline. Nice to have: Experience selling conversational AI, virtual assistant, or NLU/NLP-based solutions. Familiarity with Omilia's product portfolio (OCP, miniApps, Diamant, Pathfinder, Agentic Self-Learning). Knowledge of enterprise compliance and security standards relevant to CX platforms (PCI-DSS, HIPAA, SOC 2, ISO 27001). MBA or advanced degree. Multilingual capability (Spanish an advantage for coverage of Latin American enterprise prospects). Omilia Note - Contribute actively and effectively as an integrated team member. - Act as an Omilia ambassador in all interactions.

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Responsibilities

Lead and develop a high-performing team of Account Executives to drive net-new revenue and expand Mid-Market accounts across North America. Accountable for full-cycle sales performance, GTM strategy execution, and executive sponsorship of strategic deals in regulated verticals.