Director Value and Strategy Advisory

Talkdesk; Chicago (IL); On-site; USD 288,000 - 432,000; Full time

Benefits offered by this job

Health Insurance

401(k) plan

Uncapped paid time off

14 paid holidays annually

Job summary

Talkdesk seeks a Strategy and Value Senior Consultant in Chicago to act as a strategic advisor across the sales organization and lead business cases for strategic deals. Candidates should have 7–12 years of management consulting experience and a deep understanding of business case construction. Strong coaching and presentation skills are essential. The role involves engaging directly with C-suite executives to articulate substantial value opportunities, with a pay range of $288,000 - $432,000, along with extensive benefits.

Qualifications

• 7–12 years of experience in management consulting or related advisory functions.
• Deep expertise in business case construction and cost center economics.
• Strong coaching instincts to build capability in others.

Responsibilities

• Advise Account Executives on deal strategy and value conversations.
• Lead pre-sales teams in business process discovery.
• Construct and deliver executive-level business case presentations.

Skills

Management consulting

Value engineering

Enterprise presales strategy

Coaching

Financial modeling

Executive presentation

Job description

About the Role

As a Strategy and Value Senior Consultant, you operate as both a force multiplier across the sales organization and a direct strategic resource on our most strategic deals. In the first mode, you work across the deal lifecycle, advising Account Executives on deal strategy, shaping how they approach value conversations, and coaching them on the effective use of our proprietary value modeling platform. You build their capability to develop credible value hypotheses and deliver compelling early‑stage presentations independently, expanding the organization's overall capacity to sell on value rather than features. In the second mode, for our most complex and strategically significant opportunities, you lead pre‑sales teams’ on‑site business process discovery, own the formal business case end‑to‑end, and deliver executive‑level presentations directly to C‑suite economic buyers. The role works across industry‑aligned sales teams, but is expected to develop industry‑specific knowledge and conversancy to evidence credibility with buying executives. Central to the role is a deep understanding and dexterity in identifying where and how traditional automation, AI, and agentic AI add measurable customer‑C‑suite relevant business value in the customer experience space. The role reports to the Vice President of Presales Strategy and Solution Engineering and is closely aligned with Regional Sales Vice Presidents and the Americas Senior Vice President of Sales. The role is located in and supports deals primarily in North America.

What You’ll Do

Deal Strategy Advisory

• Engage early in the sales cycle as a strategic advisor to Account Executives (AEs), helping them assess deal structure, identify economic and organizational decision dynamics, and develop a winning approach before the opportunity is fully formed.
• Advise on stakeholder mapping, competitive positioning, and the sequencing of value conversations to establish favorable evaluation criteria ahead of formal RFP or executive review processes.
• Contribute to account planning, pipeline reviews, and deal qualification sessions—providing an informed perspective on deal health, strategic risk, and the levers most likely to accelerate or stall a decision.
• Guide AEs on cost‑of‑delay and cost‑of‑inaction framing as a tool for creating urgency with economic buyers without resorting to discount‑driven pressure.

AE Coaching & Value Tool Enablement

• Coach AEs on the use of our proprietary business case modeling tool for early‑stage value hypothesis development—building their confidence and fluency so they can lead initial value conversations independently.
• Review and provide structured feedback on AE‑developed value models and presentations, ensuring analytic credibility, accurate assumption‑setting, and appropriate calibration of projected outcomes.
• Contribute to repeatable coaching frameworks, value hypothesis templates, and discovery conversation guides that raise the baseline capability of the sales team across verticals.
• Act as an internal resource and escalation point when AEs encounter challenging financial questions, executive objections, or modeling scenarios that exceed their current capability.

On‑Site Discovery & Value Opportunity Identification (Strategic Deals)

• Lead on‑site business process discovery engagements at our most strategic accounts—facilitating structured workshops and executive interviews designed to surface operational inefficiencies, cost drivers, and high‑priority business outcomes.
• Lead team mapping current‑state processes across relevant operational domains with the rigor of management consults, producing a prioritized inventory of value potential that is analytically grounded and commercially actionable.
• Synthesize discovery findings into structured outputs that serve as the foundation for the formal business case and inform the broader deal strategy.

Business Case Modeling (Strategic Deals)

• Own end‑to‑end construction and delivery of formal business cases on priority accounts using our proprietary modeling platform and bespoke analyses to customer's specific financial context and decision criteria.
• Build models that withstand CFO‑level scrutiny—grounded in customer‑validated data, benchmarked against industry norms, and structured around the financial logic that governs capital allocation decisions in large enterprises.
• Maintain and evolve vertical‑specific benchmark libraries, value hypothesis frameworks, and cost‑of‑inaction narratives that support both your own work and the broader AE coaching program.

Executive Presentations (Strategic Deals)

• Lead the design and delivery of executive‑level business case presentations for C‑suite audiences—CEOs, CFOs, COOs, Chief Customer Officers and SVP of Customer Experience—on our highest‑priority opportunities.
• Structure presentations as strategic advisory narratives, not product pitches, positioning the business case within the customer's broader operational and financial priorities.
• Anticipate and pre‑empt executive objections through scenario analysis, sensitivity framing, and risk‑adjusted return modeling that gives economic buyers the confidence to commit.

What You Bring

• 7–12 years of experience in management consulting, value engineering, enterprise presales strategy, or a closely related advisory function within B2B software or technology sales.
• A clear track record of operating in both a coaching/advisory capacity and as a direct delivery lead— you are equally effective developing others and delivering yourself.
• Deep expertise in business case construction: P&L dynamics, cost center economics, capital allocation logic, and the financial frameworks that drive enterprise budget decisions.
• Demonstrated experience leading on‑site discovery engagements—facilitating executive and operational interviews, mapping operational processes, and translating qualitative findings into quantified value opportunity assessments.
• Executive presence sufficient to command credibility as a peer to CXOs, and senior operational leaders—in both formal presentations and working‑session dynamics.
• Strong coaching instincts: you know how to meet AEs where they are, build their capability progressively, and give feedback that sticks.
• Proficiency with advanced financial modeling and the ability to rapidly master proprietary platforms; strong command of executive presentation design.
• Vertical fluency in at least one relevant domain—contact center operations, customer experience technology, financial services, healthcare, or retail.

Preferred Qualifications

• Management consulting or similar background with exposure to operational transformation, process redesign, or technology‑enabled change programs.
• A track record of successful Fortune 2000 enterprise‑class B2B sales success.
• Experience identifying and articulating the value opportunities, such as cost, quality, and speed, of AI and agentic in business process improvement and redesign.
• Familiarity with contact center / customer experience workforce economics, customer operations cost structures, or AI‑enabled automation business cases.
• Experience supporting value realization programs post‑sale, creating a feedback loop between promised and delivered outcomes.

Pay and Benefits

Pay Range (OTE Pay): $288,000 - $432,000

Other Types of Pay: Based on level and role, the employee may be eligible for long‑term incentives in the form of equity and short‑term incentives of either bonus or commission.

Health Insurance: Medical, Dental, Vision, Life and Disability Insurance, Employee Assistance Program (EAP).

Retirement Benefits: 401(k) plan.

Paid Time Off: Uncapped paid time off program, subject to manager approval and consistent with business needs.

Paid Holidays: 14 paid holidays each year.

EEO and Equal Opportunity

We will hire, promote, work along, cheer for, bond with, and warmly welcome into the Talkdesk family all persons without regard to ethnic and racial identity, indigenous heritage, national origin, religion, gender, gender identity, gender expression, sexual orientation, age, disability, marital status, veteran status, genetic information, or any other legally protected status.

Talkdesk is a registered 501(c)3, and we are committed to doing business responsibly in a sustainable, inclusive, and ethical manner. We endorse equal opportunity practices. All applicants and employees are treated in line with federal, state, and local anti‑discrimination laws.