Technical Sales Lead

Bigbear.ai

18h

About The Position

Ask Sage (BigBear.ai company) is seeking a Technical Sales Lead to own, deepen, and expand our most critical customer relationships across the Department of Defense and Federal agencies. This is not a net-new logo acquisition role. This is a strategic, relationship-driven position focused on maximizing the value Ask Sage delivers to our existing customers and maximizing the revenue we generate from those partnerships over time. You will serve as the primary post-sale relationship owner for a portfolio of established accounts. Your mission is to ensure every customer realizes the full potential of the Ask Sage platform, identify and execute expansion opportunities, and drive measurable revenue growth within your book of business. You will be the trusted advisor our customers rely on: the person who understands their mission, anticipates their needs, and ensures Ask Sage remains indispensable to their operations. This role is critical to Ask Sage's growth strategy. While our Sales Executives focus on acquiring new business, you will be responsible for the long-term health, retention, and expansion of the accounts that form the foundation of our revenue base. You will be tasked with turning satisfied customers into strategic partners.

Requirements

3+ years of sales, account management, or strategic relationship management experience, with a demonstrated track record of growing revenue within existing accounts, not just maintaining them.
Minimum 2 years of experience selling software or SaaS solutions to the Department of Defense, Intelligence Community, or Federal agencies. You understand the procurement landscape, the budget cycle, the decision-making hierarchy, and the cultural nuances of selling into government.
Deep experience in account expansion and relationship-driven revenue growth. You know how to identify whitespace and build strong relationships within large, matrixed organizations.
A strong understanding of Generative AI, large language models, and SaaS platforms. You don't need to be an engineer, but you must be able to speak credibly about AI capabilities, use cases, and technical differentiation at the executive level.
Exceptional communication and interpersonal skills. You are equally effective in a one-on-one conversation with a program manager and a boardroom presentation to a Flag Officer or SES.
CRM proficiency. You are disciplined in maintaining accurate, up-to-date records of all account activity, pipeline, and customer intelligence.
A bias toward action and ownership. You operate with the urgency, autonomy, and accountability that a high-growth company demands.
Ability to travel to customer sites and company events as needed.

Nice To Haves

The ability to identify and follow up on leads.

Responsibilities

Serve as the primary post-sale point of contact for a portfolio of existing DoD, Federal, and commercial accounts.
Build deep, trust-based relationships with stakeholders at every level, from end users and program managers to senior leaders and executives, ensuring long-term satisfaction, retention, and loyalty.
Identify, develop, and close upsell, cross-sell, and platform expansion opportunities across your book of business.
Map organizational structures, understand mission requirements, and uncover new use cases that extend Ask Sage's footprint within each account.
Consistently meet or exceed quarterly and annual expansion revenue targets.
Proactively monitor customer satisfaction, adoption trends, and engagement signals across your portfolio. Identify and mitigate churn risks before they materialize.
Own renewal conversations and ensure continuity of service and contract value.
Maintain industry-leading retention rates across your entire book of business.
Develop and maintain comprehensive account plans for each customer, outlining growth strategies, key stakeholders, competitive dynamics, risk factors, and revenue targets.
Plan and execute structured QBRs with each customer to review platform adoption, usage metrics, ROI, and future roadmap alignment.
Use QBRs as a strategic tool to reinforce value, surface expansion opportunities, and strengthen executive sponsorship.
Take direct ownership of net revenue retention and growth within your assigned accounts.
Drive measurable increases in account value year-over-year through disciplined upsell, cross-sell, and platform adoption initiatives, ensuring that every account in your portfolio is expanding, not contracting.
Establish and track account health metrics including customer satisfaction, platform adoption depth, and executive engagement.
Demonstrate quarter-over-quarter progress in strengthening the strategic relationship between Ask Sage and each customer in your portfolio.
Work closely with Product, Marketing, and Billing teams to translate customer feedback into product improvements, ensure seamless delivery, and co-develop content, case studies, and collateral that reinforce Ask Sage's value proposition.
Advocate for your customers within Ask Sage.
Ensure their mission needs, feedback, and priorities are represented in product roadmap discussions, go-to-market strategy, and company-wide decision-making.
Keep all account activity, pipeline data, expansion opportunities, and customer intelligence meticulously documented in the appropriate CRM.
Deliver accurate forecasts and pipeline reports to sales leadership.