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Teaching Strategies is an innovative edtech organization focused on connecting teachers, children, and families. As front runners in the early childhood education market, we build dynamic, top-quality digital products that integrate all of the essential elements of a high-quality solution: curriculum, assessment, professional development, and family engagement. We are building a team of results-oriented individuals who will thrive in a collaborative, work-hard/play-hard culture. We pride ourselves on the impact we have on the early childhood field through supporting teachers who are doing the most important work there is, teaching children to become creative, confident thinkers.
Position OverviewThe Senior Manager, Deal Desk & Pricing Strategy is a newly created role within the Revenue Operations team. This person will own the commercial architecture that drives ARR growth at Teaching Strategies - from pricing strategy and packaging design to deal structuring and discount governance. We are looking for someone who thinks in ACV and ARR, and sees pricing as a key driver of durable revenue growth. The role has two complementary mandates. First, you will own pricing and packaging strategy: analyzing product-market fit of our bundles, building data-driven pricing models, evaluating competitive positioning, and recommending changes that increase average deal value and margin. Second, you will build and operate the Deal Desk function: establishing approval workflows, structuring non-standard deals, facilitating executive deal reviews, and creating the guardrails that let the sales team move fast without giving away the house. This is a high-visibility, high-impact role with one direct report – an RFP specialist who manages the end-to-end RFP/RFI response process. You will work directly with the CEO, CFO, and sales leadership on the deals that matter most. You will report to the VP of Revenue Operations and partner closely with Sales, Finance, Partner Success, and Legal.
Specific Roles & Responsibilities:
Pricing Strategy & Packaging
- Own the pricing architecture for Teaching Strategies’ product portfolio, including curriculum, assessment, professional development, and platform solutions
- Develop and maintain pricing models that optimize for ACV growth, margin improvement, and competitive positioning across K-12 public districts, State education agencies, private childcare, and Head Start segments
- Lead bundling and packaging strategy - evaluate current bundles for attach rate performance, identify whitespace for new packages, and model revenue impact of proposed changes
- Conduct competitive pricing analysis and maintain a pricing intelligence framework that informs sales positioning and product roadmap decisions
- Build the business case for pricing changes, including scenario modeling, sensitivity analysis, and revenue impact projections for executive and board-level review
- Establish and maintain discount governance - define standard discount tiers, escalation thresholds, and approval authorities by deal size and type
Deal Desk Operations
- Build and operate the Deal Desk function from the ground up - define processes, SLAs, approval matrices, and escalation paths for non-standard deals
- Structure complex and high-value deals including multi-year agreements, enterprise bundles, custom pricing, and strategic partnerships
- Facilitate Big Deal Reviews for opportunities ≥$200K, including pre-review preparation, qualification assessment, commercial term review, approval coordination, and post-review action tracking
- Serve as the commercial advisor to the sales team - coach reps and managers on deal structuring, negotiation strategy, and value-based selling during active deal cycles
- Ensure quote accuracy and compliance by reviewing proposals, validating pricing configurations in Salesforce, and catching errors before quotes reach customers
- Track and report on deal quality metrics - discount rates, ACV, deal cycle time, win rates by price point, average deal value trends, and exception frequency
Cross-Functional Impact
- Partner with Finance on revenue recognition, margin analysis, and compensation plan alignment with pricing strategy
- Collaborate with Business Applications to ensure Salesforce quoting workflows, approval processes, and CPQ configurations reflect current pricing rules and discount authorities
- Work with Legal to standardize contract terms, define acceptable commercial concessions, and streamline the redline process for enterprise deals
- Inform Partner Success on implementation capacity constraints, ensuring commercial commitments align with delivery capabilities
- Partner with Product and Marketing to align pricing with product launches, packaging updates, and go-to-market campaigns
Qualifications:Required:
- 7+ years of experience in Deal Desk, Pricing Strategy, Revenue Operations, or Sales Operations within a B2B SaaS environment
- 3+ years in a people management or senior individual contributor role owning pricing or deal structuring end-to-end
- Demonstrated experience building or scaling a Deal Desk function, including approval workflows, discount governance, and executive deal reviews
- Strong analytical and financial modeling skills - comfort building pricing models, scenario analysis, and business cases in Excel or equivalent tools
- Deep understanding of SaaS pricing models (per-seat, per-site, tiered, usage-based), multi-year deal structures, and subscription economics
- Experience with Salesforce CRM and CPQ (or equivalent quoting tools); ability to translate pricing strategy into system configuration requirements
- Excellent communication skills with the ability to present pricing recommendations and deal structures to C-level stakeholders
- Track record of measurably improving deal outcomes: ACV growth, discount compression, win rate improvement, or deal cycle acceleration
Preferred:
- Experience in EdTech, K-12, or government/public sector sales environments where procurement processes, grant funding, and RFP requirements are common
- Experience at a PE-backed company with exposure to board-level financial reporting and value creation planning
- Familiarity with MEDDPICC or similar deal qualification methodologie
- Experience with pricing tools or custom-built pricing engines
- MBA or advanced degree in a quantitative discipline
Why Teaching Strategies
At Teaching Strategies, our solutions and services are only as strong as the teams that create them. By bringing passion, dedication, and creativity to your job every day, there's no telling what you can do and where you can go! We provide a competitive compensation and benefits package, flexible work schedules, opportunities to engage with co-workers, access to career advancement and professional development opportunities, and the chance to make a difference in the communities we serve.
Let's open the door to your career at Teaching Strategies!
Some additional benefits & perks while working with Teaching Strategies
Teaching Strategies offers our employees a robust suite of benefits and other perks which include:
- Competitive compensation package
- Employee Equity Appreciation Program
- Health and wellness insurance benefits
- 401k with employer match
- Flexible work environment
- Unlimited paid time off (which includes paid holidays and Winter Break)
- Paid parental leave
- Tuition assistance, professional development, and opportunities for career growth
- Best in class technology equipment for every employee
- Penthouse suite in downtown DC seconds away from Washington Nationals Stadium and Audi Field
Teaching Strategies is an equal opportunity employer and is committed to fostering a workplace where everyone can thrive.
