Vice President of Enterprise Sales/Portfolio Management

ABOUT DECISELY:

At Decisely, we are on a mission to revolutionize the InsurTech industry by delivering innovative solutions that genuinely make a positive difference for our clients and our organization. As a client-centric company, we are deeply committed to delivering exceptional customer service and building strong, lasting relationships with our clients. We seek passionate, service-driven individuals who share our dedication to putting clients first. We believe in creating a workplace where everyone feels valued, empowered, and inspired to bring their best selves to work, while contributing to a service-oriented environment that ensures our clients' success.

POSITION SUMMARY:

Owns enterprise new logo acquisition, expansion, and overall portfolio performance across the commercial book of business. Accountable for building and scaling a disciplined enterprise sales and portfolio management engine—defining ICP and segmentation, establishing account prioritization frameworks, aligning territory/coverage models, and ensuring pipeline health translates into predictable revenue outcomes.

Leads structured enterprise deal governance from qualification and stakeholder mapping through pricing strategy, negotiation, and close, while protecting margin integrity and implementation readiness. Responsible for optimizing the commercial portfolio by monitoring product mix, unit economics, concentration risk, and client profitability, ensuring resource allocation aligns with growth and contribution targets.

Oversees forecast accuracy, conversion performance, and sales productivity, installing a strong operating cadence (pipeline inspection, QBRs, win/loss analysis) that improves win rates and reduces sales cycle variability. Partners closely with Market GMs, Carrier Solutions, Client Experience, and Revenue Operations to ensure clean handoffs, durable client outcomes, and improved net revenue retention.

KEY RESPONSIBILITIES:

Enterprise sales strategy & execution

• Build and run the enterprise sales motion: ICP, segmentation, territory/coverage (if applicable), target account plans, and stage definitions.
• Drive pipeline generation, deal strategy, pricing/packaging alignment, and consistent closing execution.

Portfolio management & profitable growth

• Manage the commercial portfolio for growth and margin: segment performance, product mix, cost-to-serve considerations, and risk concentration.
• Partner with Finance/RevOps to align targets, capacity, and unit economics.

Forecasting & operating cadence

• Own forecast accuracy and weekly/monthly performance rhythm (pipeline inspection, QBRs, win/loss, and conversion diagnostics).
• Establish dashboards that identify leading indicators and enable fast interventions.

Cross-functional alignment for enterprise delivery

• Ensure enterprise deals are implementation-ready: clean discovery, realistic commitments, and tight handoffs to program/onboarding teams.
• Partner with Client Experience to reduce onboarding friction and protect retention.

Team leadership & talent development

• Coach and develop enterprise sellers and/or sales leaders; hire for consultative, disciplined selling.
• Set clear expectations for activity standards tied to outcomes (not busywork), especially in a remote model.

CORE COMPETENCIES:

Enterprise Sales Leadership

• Builds repeatable enterprise motions and strong deal governance (MEDDICC/Challenger-style rigor as appropriate).
• Elevates sales capability through coaching, call review, and disciplined inspection.

Portfolio Strategy & Business Acumen

• Understands unit economics, margin drivers, and product mix; makes tradeoffs for profitable growth.
• Uses segmentation and performance data to allocate effort and investment.

Forecasting & Revenue Operations Discipline

• Creates accurate forecasts through clear definitions, inspection, and CRM integrity.
• Diagnoses funnel leakage and systematically improves conversion rates.

Cross-Functional Orchestration

• Aligns Sales, Marketing, Program Management, and Client Experience around shared outcomes.
• Drives clean handoffs, reduces rework, and resolves friction fast.

Executive Presence & Influence

• Communicates clearly with senior stakeholders; escalates with options and implications.
• Represents Commercial Success credibly with partners, clients, and internal leadership.

REQUIRED QUALIFICATIONS:

• 10+ years in B2B enterprise sales leadership; 5+ years leading teams or a multi-region/segment book
• Experience with complex/consultative sales cycles (multiple stakeholders, regulated environments preferred)
• Demonstrated portfolio leadership: segmentation, performance management, and resource allocation
• Strong forecasting, pipeline analytics, and CRM discipline (Salesforce/HubSpot or similar)
• Benefits/Insurtech/adjacent regulated industry experience preferred
• Life, Health, Accident/Sickness license required
• Comfort with reporting, metrics, and process adherence (Excel/Sheets, CRM/ticketing tools)
• Must be able to work well with partnering departments (Growth Shared teams, Corporate Services, Development)

TO BE SUCCESSFUL IN THIS ROLE:

• Build a predictable enterprise pipeline engine with clear ICP and account targeting
• Improve forecast accuracy and pipeline hygiene through a consistent operating cadence
• Increase win rate by tightening qualification, deal strategy, and stakeholder mapping
• Protect margin and delivery outcomes by ensuring enterprise deals are implementation-ready
• Create a high-performance remote sales culture with clear standards, coaching, and accountability

PHYSICAL DEMANDS:

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. While performing the duties of this job, the employee is regularly required to stand; walk; sit; use hands to finger, handle, or feel; reach with hands and arms; and talk or hear. Specific vision abilities required by this job include close vision, color vision, and ability to adjust focus. Ability to travel independently to clients; some air travel may be required. To foster collaboration and team spirit, and although this is primarily a remote position, there is occasion when you will be required to come into the office for meetings and team building activities as well as travel to our various offices for meetings and team building activities.

WORK ENVIRONMENT & ENVIRONMENTAL CONDITIONS:

 The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The noise level in the work environment is usually moderate. There is no or very limited exposure to physical risk.