It’s time to tend to what comes next.

You’ve planted the seeds of meaningful impact — but lately, it feels like the climate around you is shifting.

Funding priorities have changed. Long-time donors are moving in new directions. And while your team is dedicated and mission-driven, the systems that once supported your growth are starting to show strain. You’re trying to keep things thriving, but the soil — your strategy, your structure, your funding model — needs renewal.

At Boss Insights, we help organizations in transition pause, assess, and replant with intention. Whether you’re navigating a funding drought, preparing for new growth, or redesigning how your team works together, we help you strengthen roots before reaching for the next harvest.

Because sustainability isn’t about doing more — it’s about cultivating what matters most, and creating the conditions for your mission to keep growing.

Strategic Guidance for Seasons of Change

Work directly with founder Whitney Kippes to ensure you take the right path.

  • Organizational Strategy Assessment

    Clarify what’s growing — and what’s not.

    Before you can nurture the next phase of growth, you need a clear picture of your current landscape. In this two-day intensive, Whitney works directly with your team to pause and take stock — of your goals, funding streams, and internal capacity.

    Together, you’ll surface what’s thriving, identify what needs pruning, and outline concrete next steps to strengthen your organizational foundation. The result: a focused roadmap that supports both stability and sustainable growth.

  • Seasonal Growth Planning

    Design your next season of growth.

    Whitney helps clients reimagine how your teams approach business development. Through facilitated planning sessions, tailored frameworks, and practical guidance, she helps you strengthen positioning, build smarter pursuit systems, and adapt to a changing funding environment.

    Whether you’re refreshing your strategy or rebuilding your BD process from the ground up, this work ensures your organization grows with clarity and purpose — not burnout and guesswork.

  • Regenerative Leadership Coaching

    Help your people bloom in any weather.

    When teams are stretched thin or leaders are navigating change, clarity and connection can get lost. Whitney’s coaching brings those back into focus. She works one-on-one with executives and teams to rebuild confidence, improve communication, and reignite engagement.

    Through a mix of coaching, facilitation, and reflection, leaders leave with renewed purpose — and teams gain the alignment they need to grow together.

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Embedded Expertise for Every Season

Accessing proven fractional business development and project management expertise is more valuable than ever. Regardless of whether your organization is paring back, planting seeds, or harvesting recent wins, our team is here to help.

  • Cultivating New Opportunities

    Keep your pipeline thriving.

    Our embedded consultants provide part-time or seasonal business development support — helping you maintain capture efforts, strengthen partnerships, and pursue opportunities with consistency. It’s like having an experienced BD strategist on your team, without the full-time commitment.

  • Proposal Cultivation Support

    Navigate smoothly from seed to submission.

    From capture to submission, our consultants bring structure, strategy, and storytelling expertise to your proposal process. Whether you need red-team reviews, pricing support, or full proposal management, we help you deliver polished, competitive bids that reflect your organization’s best work.

  • Plant Successful New Projects

    Set your next project up for success.

    When a new award lands, our team helps you lay the groundwork for a smooth launch. From start-up planning and staffing to compliance systems and reporting structures, we ensure your projects are rooted in clarity and accountability — ready to thrive long after start-up.

Frequently Asked Questions

Understand fractional team support.

  • What is fractional support and what are the benefits?

    In the simplest terms, a fractional support agreement allows your team to pre-pay for a set number of consulting hours in advance. We are able to guarantee our availability and provide a wide range of services to your team at an agreed rate over a set period of time. A fractional support agreement offers a few concrete advantages:

    • You have our guaranteed availability for a set number of hours each month.
    • You can budget your monthly expenses based on the retainer rate.
    • Longer-term support means we can get to know your systems and processes.
    • Our fractional support clients take priority over other requests for surge support.
  • What services are included?

    Generally speaking, fractional support is the most adaptable way in which we work. The specific scope of work can flex to respond to the most urgent or important needs of your team. For example, current fractional support clients have included a set number of hours for:

    • Assisting in building a business development strategy
    • Leading relationship management or partnership development
    • Supporting cost proposal development and budget reviews
    • Serving in proposal team roles, as managers or coordinators
    • Conducting landscape or capture research

    Our goal is to support your team in the specific roles where we will provide the most value and return on investment.
  • How long does a typical assignment last?

    Short-term support, such as our two-day strategy assessment or business development strategy support are tailored to the specific needs of the client. A fractional support agreement is best suited when you expect a need for support over three months or more. We have found this is the minimum amount of time it takes to get comfortable working together and see the real benefits of embedded support. Even if you need support for over three months, an initial three-month agreement provides a good opportunity to check in to determine if the monthly baseline number of hours still fits your needs.

  • What technical or programmatic areas do you support?

    Our team of proposal writers and design facilitation experts represent a range of technical sector areas including agriculture, economic growth, education, entrepreneurship, food security, governance, humanitarian assistance, and health.

  • How far in advance do you get booked up?

    We recommend that you reach out for bid support as soon as you know that you may need support. The sooner that we know, the better. During our busy seasons, we can be booked up three or more months in advance.

    Due to the high volume of requests for USDA proposal support and our knowledge that competition is increasingly fearce, we recommend reaching out in December for the upcoming proposal season (typically Jan-June) to ensure availability.

  • How are your rates structured?

    We price each assignment based on the mix of services anticipated and the specific consultants who will support your team. For example, the rate for fractional copy editing support would be lower than that for an assignment providing leave coverage for a senior business development leadership role. Rates for a 40-hour per month retainer typically fall between $3,600 and $6,000. Shorter term assignments typically bill at a fixed hourly rate, typically between $100 and $200 per hour.

  • What's your win rate?

    Our win rate sits between 10-20 points above the industry standard of about 30%. So many factors can influence the probability of winning for the individual opportunity you’re considering, though! We’re always here to talk strategy if you’re working to increase your organizational win rate.

  • How do you navigate potential conflicts of interest?

    With the nature of our business, Boss Insights is sometimes approached by competing clients to support the same funding opportunity. Generally, we try not to provide the same role for two directly competing clients. When we are supporting competitors, we create internal communication between consultants and staff working on those opportunities. Additionally, we try to be as transparent as possible while not disclosing competitive information.

Understand coaching for staff retention.

  • Why do social impact professionals need coaching?

    Because doing good work doesn’t mean it’s easy work. Social impact professionals are often navigating complex systems — balancing big missions, limited resources, and the emotional weight of caring deeply about the outcomes. Coaching creates space to pause, reflect, and realign. It helps leaders and teams clarify priorities, strengthen communication, and make intentional choices instead of reacting to constant urgency. For individuals, coaching can mean rediscovering purpose, setting boundaries, or building confidence in new leadership roles. For organizations, it means healthier teams, stronger retention, and a culture where people can thrive — not just endure. Coaching isn’t about fixing what’s broken; it’s about cultivating growth, resilience, and clarity in work that truly matters.

  • How can coaching help my team or staff members?

    Organization-sponsored employee coaching can be a valuable support system for staff members. We most frequently have employers sponsor coaching in two situations:

    • When an employee is struggling to achieve performance-related goals.
    • When an organization is concerned about retaining a highly valued employee who is showing signs of burnout.

    In either situation coaching can help an employee by providing a neutral third-party to meet regularly, foster self-awareness, discuss challenges and goals, and help them learn, develop, and refine skills.

  • How does individual coaching work?

    In order to create the future you want, we start with defining what you want to achieve and what improvements need to be made if you want to reach and exceed your long-term goals. We'll get into your motivation and why this goal is important to you, explore your core values, and conduct a leadership growth assessment.

    Then, your coach asks powerful questions to guide you while you try different approaches and test out new ways of thinking about old problems. Our goal in working together should be to find out what works for you—not what worked for someone else.

    Coaching relies on asking questions and observing. This lets your coach to facilitate inquiry, allowing you the opportunity to address specific or individual issues. The goal is to give you the perspective and action plans that will continually support you in your personal or career growth long after our work together is complete.

    This whole process is held within an environment designed to prioritize trust, safety, and confidentiality, in alignment with the International Coaching Federation Code of Ethics.

  • How long does a typical coaching engagement last?

    Most coaching partnerships span 3–6 months, with sessions every two to three weeks. This gives participants time to apply new insights between sessions and see measurable progress. We also design shorter coaching intensives or team-based sessions around key organizational milestones or leadership retreats.

  • What outcomes can coaching achieve?

    While outcomes vary, common results include improved communication and collaboration, increased confidence in decision-making, stronger staff retention, and a clearer sense of strategic focus. We also provide reflection tools and progress check-ins so HR and leadership teams can see tangible impact over time.

  • What about confidentiality?

    Coaching conversations are confidential to protect trust and honesty. When organizations sponsor coaching, we establish clear boundaries from the start — often sharing broad themes or development goals (with the participant’s consent) while keeping personal details private. This balance ensures accountability without compromising candor.

  • Can coaching be combined with other support from Boss Insights?

    Yes. Many organizations pair coaching with strategy sessions or team facilitation to ensure that individual insights align with organizational priorities. This integrated approach helps create sustainable change — not just personal growth, but systemic improvement across teams and leadership structures.

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