Vice President of Enterprise Sales/Portfolio Management

Decisely•Alpharetta, GA

9h•Remote

About The Position

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.

Requirements

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)

Nice To Haves

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

Responsibilities

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.
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.
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.
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.
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.
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.