Expanding the stack

Close: Capabilities to drive sales, retain customers, and upsell

In this phase, we look at tools and capabilities that improve efficiency, optimize interactions, and enhance the customer experience to close deals faster and with greater success.

The "Close" phase focuses on moving leads through the funnel, converting them into customers, and retaining them through upsell and ongoing engagement. In this phase, we look at tools and capabilities that improve efficiency, optimize interactions, and enhance the customer experience to close deals faster and with greater success.


1. Demo and Calendaring

What problem does it solve?

Scheduling and managing product demos or sales meetings can become a logistical nightmare, especially as the volume of leads increases. Demo and calendaring tools solve the problem of automating the process of booking time with prospects, reducing back-and-forth communication and helping sales teams stay organized.

How it interacts with the stack:

demo and calendaring
  • CRM Integration: Integrates with CRM systems to automatically log meetings, demos, and interactions, ensuring all data is up-to-date. While some rely on a direct data connection, others use embedded links in email templates alongside the CRM’s built-in calendar integration to sync events with minimal overhead.
  • Email Marketing: Works with email marketing platforms to include scheduling links in emails and campaigns.
  • Video Conferencing: Syncs with video conferencing tools (e.g., Zoom, Microsoft Teams) to automatically generate meeting links.

To Tool or Not to Tool?

We’re firm believers everyone should have a calendaring tool in 2025. Manual scheduling is possible for smaller teams or when handling a limited number of high-touch clients but these tools are affordable enough that even non-professionals should use them. That said, many CRMs offer light scheduling services, so the real tooling question is whether you use the scheduling feature in your CRM or consider adding to your stack a dedicated tool. If you do use a third party, make sure to integrate with video conferencing tools, and sync appointments with your CRM. 

Typical Mistakes People Make:

  • Overbooking or double-booking: Failing to sync calendars properly can lead to scheduling conflicts.
  • Not customizing availability: Lack of proper settings can result in inefficient scheduling, with team members getting booked for the wrong types of meetings.
  • Ignoring time zone differences: Not accounting for different time zones can cause confusion and missed meetings.

Various vendor choices & pricing

demo and calendaring vendors

2. Sales Enablement

What problem does it solve?

Sales enablement addresses the challenge of equipping sales teams with the resources, information, and training they need to effectively close deals. Sales teams often struggle with accessing the right content, staying updated on product changes, or maintaining consistency in their messaging.

How it interacts with the stack:

sales enablement
  • CRM Integration: Syncs with CRM systems to ensure sales reps have access to up-to-date customer information and sales content.
  • Marketing Automation: Integrates with marketing automation tools to align content creation and distribution with sales needs.

To Tool or Not to Tool?

Smaller teams may manage sales enablement manually, using shared folders or basic content repositories. Regular training can be conducted through workshops and ongoing coaching sessions. As your team grows, tools like Seismic, Showpad, or Highspot provide a centralized hub for content management, product updates, and sales training. These platforms automate the delivery of resources based on the sales stage and track usage to ensure teams are engaging with the most relevant materials.

If sales enablement isn’t improving performance:

  • Are sales reps finding the content they need? Review how content is organized and whether it's easy for sales teams to access the right material for each stage of the sales process.
  • Are you providing continuous training? Regular updates and ongoing training ensure that reps stay knowledgeable about product changes or market shifts.
  • Is the feedback loop between sales and marketing strong? Ensure that sales teams provide feedback to marketing so that content and resources stay relevant and effective.

Typical mistakes people make:

  • Overloading reps with content: Too much content or poorly organized resources can overwhelm sales teams.
  • Neglecting continuous training: Sales teams need regular updates to stay sharp, especially in industries with rapid product changes or competition.
  • Ignoring feedback: Without a feedback loop between sales and marketing, enablement content may not address the actual needs of the sales team.

Various vendor choices & pricing

sales enablement

3. Proposal Generation and E-Signature

What Problem Does It Solve?

Creating and managing sales proposals manually can be time-consuming and prone to errors, particularly as deals get more complex. Proposal generation tools help automate the creation of accurate, professional proposals, while e-signature tools streamline the contract process.

How it interacts with the stack:

proposal and e-signature

These tools integrate with CRMs to automatically pull in relevant deal information and track the status of proposals, helping sales teams manage their pipeline more efficiently.

To Tool or Not to Tool?This is a similar category where it almost always makes sense to have a tool from the start. The cost is low, and having the protection of a great e-signature tool is very critical. The broader question is whether you combine your e signature and your CPQ (or proposal creation manager) into one. There are some tools that only handle the generation and management of the deal memos, and others that only handle the e-signature. These two tools must work together and we believe over time these two will merge. Then, there are a related but different class of tools called CLMs which actually manage the contract signing process. These are typically beneficial when you’re often creating custom terms and conditions for each client (something you’d ideally avoid long-term but is often necessary as an early start-up selling to large enterprises).

If your proposal process is still inefficient:

  • Are your templates optimized? You shouldn’t ever start from a blank document for proposals. All should be templatized and automated.
  • Is the approval process streamlined? Ensure that your tool allows for quick approvals, reducing bottlenecks.
  • Are you tracking proposal status? If you’re not using the tool’s analytics or CRM integration, you might be missing insights into when proposals are viewed and which deals are stalling.

Typical Mistakes People Make:

  • Not optimizing templates: Outdated templates can lead to errors or missed opportunities for customization.
  • Ignoring approval workflows: Complex approval processes can slow down proposal generation.
  • Failing to track proposal status: Without visibility into when a prospect opens or reviews a proposal, sales teams may miss follow-up opportunities.

Various vendor choices & pricing

proposal vendor comparison

4. Customer Support Systems

What problem does it solve?

Once a customer has been acquired, providing ongoing support is key to retaining them and identifying upsell opportunities. Customer support systems ensure that customer issues are resolved quickly, improving satisfaction and reducing churn.

How it interacts with the stack:

customer support

Customer support tools serve as a central hub for managing all inbound inquiries, syncing data with CRM, marketing automation, and e-commerce platforms. They pull in customer details (like order history and past interactions) to give agents a 360° view, then push updates back so other teams can see support outcomes. This keeps your sales and marketing pipelines aligned with real-time customer issues, ensuring faster resolutions and a better overall experience. By centralizing every interaction, support teams can collaborate more effectively and gain insights into trends, bottlenecks, and areas for improvement. In fact, some teams consider this to be part of the “Generate/Inbound” motion, while others consider it part of the “Close” motion. In reality, it plays an important role in both.

To Tool or Not to Tool?

For smaller businesses or startups, customer support may be handled manually via email or phone calls. A shared inbox or simple ticketing system may suffice at this stage. As your business scales, tools like Zendesk, Freshdesk, or Intercom allow you to manage support tickets, track customer interactions, and integrate with your CRM to provide a holistic view of the customer journey.

If your customer support system isn’t delivering results:

  • Are tickets being routed correctly? Ensure that your routing rules are up-to-date and that tickets are being assigned to the right teams.
  • Are you tracking response times? Slow response times can frustrate customers and increase churn. Set clear SLAs and track adherence.
  • Are customer issues being resolved on first contact? Review your knowledge base and training processes to ensure that support reps are equipped to handle issues efficiently.

Typical Mistakes People Make:

  • Ignoring ticket routing rules: Incorrect routing can delay issue resolution and frustrate customers.
  • Overlooking response times: Slow responses lead to customer dissatisfaction and churn.
  • Not resolving issues on first contact: Failing to equip support teams with the right knowledge or tools can increase the time to resolution.

Various vendor choices & pricing

customer support vendors

5. Customer Success Platform

What Problem Does It Solve?

Customer success platforms help ensure that your customers are getting value from your product or service. These platforms help monitor customer health, reduce churn, and identify upsell opportunities.

How It Interacts with the Stack

customer success platform

Integrates with CRM and product analytics tools to get a complete picture of customer health and engagement.

To Tool or Not to Tool?Manual tracking via spreadsheets and CRM notes may work in early stages, but this can become inefficient as the customer base grows. As customer success becomes a focus, tools like Gainsight or ChurnZero help track customer health scores, manage customer touchpoints, and identify churn risks.

I Have It, But It Isn’t Working How I’d Like It To

  • Are you using the right data? Customer success tools rely on accurate customer engagement and product usage data.
  • Is there enough touchpoint visibility? Ensure the tool is tracking all relevant interactions between your team and the customer.
  • Are you aligning with sales? Customer success should work closely with sales to identify expansion opportunities and avoid churn.

Typical Mistakes People Make

  • Focusing too much on reactive support rather than proactive engagement.
  • Not integrating with other systems to ensure a holistic view of the customer.

Various vendor choices

Note: We’ve omitted pricing on this one as most vendors only offer custom quotes.

customer success

6. Workflow Automation Tools

What Problem Does It Solve?

Managing leads, routing data, and automating repetitive tasks across your RevTech stack can be time-consuming and error-prone. Workflow automation tools streamline these processes—such as assigning leads, updating records, syncing data between systems, and triggering alerts—so sales and marketing teams can focus on high-value work.

How It Interacts with the Stack

workflow automation tools

These platforms typically integrate deeply with CRMs (e.g., Salesforce, HubSpot), marketing automation suites, and other databases. They pull records, apply preconfigured rules or algorithms (e.g., round-robin routing, territory-based assignment), then push updated data back to keep everything in sync. Some tools also connect with internal communication platforms (Slack, Microsoft Teams) to send alerts or notifications when certain events occur (e.g., a hot lead arrives).

To Tool or Not to Tool?

  • Early-Stage: If your lead flow is simple, you might manage routing with basic CRM automations.
  • Scaling Up: Once inbound lead volume rises or you have complex rules (e.g., multiple territories, multi-field matching), dedicated workflow automation tools become essential to prevent bottlenecks and ensure data quality.

That said, many CRMs—including platforms like HubSpot, Addio, and Clarify—already offer built-in workflow or automation features (e.g., if/then branching, email triggers, lead routing rules). These native tools can cover basic processes such as automatically assigning leads, updating records based on certain criteria, or sending follow-up emails. For smaller teams or straightforward workflows, the CRM’s out-of-the-box automation might be sufficient.

A specialized third-party workflow automation tool usually becomes valuable when:

  • Cross-System Complexity: You need advanced rules that span multiple systems (e.g., CRM, marketing automation, data enrichment, finance) rather than staying within just the CRM environment.
  • Advanced Logic or Scalability: You require more sophisticated conditions, orchestrations, or volume handling than the CRM’s built-in automations can support.
  • Customization & Extensibility: Dedicated automation platforms often have larger integration libraries and more flexible “drag-and-drop” logic builders, making it easier to adapt to unique business processes.

Common Issues

  1. Overly Complex Rules: Layering too many nested conditions can cause confusion and break workflows.
  2. Dirty or Incomplete Data: If the data feeding into your workflows is poor, automation can amplify errors.
  3. Lack of Maintenance: Automated processes need periodic review to account for new products, territories, or team structures.

Typical Mistakes

  • One-Size-Fits-All Routing: Failing to tailor rules for different lead segments or channels can reduce personalization.
  • No Reporting on Automation Outcomes: Without analytics, teams can’t see if workflows are actually speeding up lead response or improving conversion.
  • Ignoring Scalability: Systems that work for a team of 10 might not be sufficient once you hit 50+ reps.

Various Vendor Choices

workflow vendors

7. Call Recording and Sales Analytics Tools

What Problem Does It Solve?

Sales conversations often contain valuable insights—from customer pain points and objections to competitor intel and upsell opportunities. Call recording and analytics tools capture these conversations, transcribe them, and use AI to surface critical data. This helps reps improve their pitches, managers coach more effectively, and leadership gauge market feedback.

How It Interacts with the Stack

call recoridng

These tools typically integrate with CRMs so recorded calls and conversation summaries get attached to the right contact or opportunity. They may also connect with video conferencing (Zoom, Google Meet) or VoIP systems (RingCentral, Aircall), automatically pulling in conversation data. Some solutions tie into coaching modules, enabling managers to highlight specific call moments for training.

To Tool or Not to Tool?

Everyone should have one of these. No reason we can see not to given the affordability unless you aren’t selling via virtual calls. That said, this is another one where some CRMs, like Clarify, have the functionality built in whereas other CRMs will need to be paired with a specialized tool.

Common Issues

  1. Poor actionability: Some tools are better than others at providing actionable insights rather than just summaries from the calls.
  2. Unhelpful insights: Some tools are better than others at providing robust insights after reviewing many calls.

If either of those are the case, it probably makes sense to consider switching tools.

Typical Mistakes

  • Failing to Tag or Categorize Calls: Makes it harder to analyze patterns or locate key moments.
  • Ignoring Coaching Opportunities: Even with transcripts, managers need to actively review calls to drive improvement.
  • Not Syncing with CRM: Losing the link between call data and deals weakens any analytics.

Standalone Various Vendor Choices (some CRMs have this in-house)

call recording vendors

These capabilities are crucial for driving sales, improving customer satisfaction, and retaining customers through upselling and support. In the next phase, we’ll focus on capabilities that ensure accuracy and alignment in reporting and analytics.

Next lesson4: Report (Accuracy): capabilities for funnel analysis, forecasting, and financial reporting