What advice would you give to someone tasked with taking the sales function up market in an existing business structure?

Good question! Taking a sales function up market in an existing business can be one of the most challenging but lucrative transformations of an organization. Often in the early days of your business and go-to-market motion you'll tend to focus on smaller, more nimble customers to validate your product-market fit and refine your go-to-market approach. During this phase, your supporting business structures of product development, finance, legal, security & compliance, etc. will mold to fit the requirements of your business at that point in time.

Wayne Gretsky famously said, "I skate to where the puck is going to be, not where it has been."

So, when it's time to go up-market, one of the most important things you need to do first, is help your supporting business structures evolve to meet you where you are headed, not where you are. 

To do that...

1) Be clear on your objectives - what does success going up-market look like in the next 90 days. Advice: be modest in your expectations, as it usually takes longer than you would have initially anticipated, and focus on the next 90 days at a time

2) Identify the gaps & be explicit about the resources you need - within your existing supporting business structures, what is required for them to evolve to meet you where you are headed?

• Product development - are they prepared to adjust the product roadmap to the needs of larger clients? what is the mechanism for recieving, triaging, and prioritizing those requests?
• Finance - are your finance policies & systems prepared to be flexible to more customized payment terms? do you have a process for completing vendor set up forms?
• Legal - do you have the resources to negotiate MSAs, DPAs, security terms, etc? do you have proper policies & documentation in place to ensure compliance with GDPR, CCPA, etc? 
• Security & compliance - do you have the necessary policies & procedures? do you have the certifications required by the new market you are serving (ISO 27001, SOC2, FedRamp, etc.) ? do you have a process for completing security questionnairs & audits?

3) Up-level your team - going up-market can sometimes mean you need different skills, experiences, and roles within your sales organization to best support your larger clients. Begin to as yourself questions like:

• Does my existing team have experience selling into larger organizations? or do I need to recruit additional talent?
• Do we need to re-segment our accounts into new territories and books of business to create better alignment?
• Does our current structure support a more mature selling motion? or do we need additional resources (customer success managers, accounts managers, solutions consultants, etc.) to take it to the next level?
• How do we develop the skills of our team and implement a more mature sales motion with concepts like territory & account planning, champion building, business case generation, etc?

4) Join as many customer conversations as you can - by getting in the field yourself, you are able to develop an intimate understanding of the common objections & gaps within your offering or go-to-market motion, and you can provide your reps more relevant direct coaching 

Here's some advice I would give to someone tasked with taking the sales function up-market in an existing business structure:

*What sales cycles are repeatable that have closed up market? 

*What hiccups did you see in that original sales cycle? 

*Competitive Landscape 

*What potential objections change and how do you sell around them differently? 

*What was the process around: Security? Legal? Procurement?  

If you haven't closed anything up-market yet in your sales org, I recommend first asking for recommendations from your current customers that are down-market. An introduction is the best way to start this process from someone who is currently spending money with you. 

Moving up-market is no easy task. It adds a great deal of complexity, precision, and requires more people, processes, workflows, and technologies to do it effectively.

This initiative must be done company wide and has to address the ongoing challenges that your target (or evolving/new target) audience must solve at a global scale. Here are a few things you’ll need to think about as you shift from a velocity to a transformation motion:

1. Historical success
1. Have you closed up market in the past?
1. Can you create a playbook around these successes?
2. What deals have we lost up market? Can we take learnings from these losses in order to adjust our sales motion, product, security, legal, etc. in order to win?
2. Product
1. Are you solving an enterprise need?
2. Are you sustainable for an enterprise wide deployment? Have you done this in the past?
3. Integrations and workflows
4. How do you differentiate in the competitive market?
3. Security
1. Configuration and posture management
2. Architecture
3. Monitoring and threat protection
4. Automated workflows
5. DevSecOps
1. SSO, SAML, authentication flows
6. Governance and risk compliance
7. System functionality and APIs
4. Marketing and Sales alignment
1. Target audience
1. Does this change as you go up market?
2. Target account list
1. Firmographic + technographic data
3. Segmentation
2. ABM (account based marketing)
3. Lean on your investors for support and guidance
4. Do you have the technologies to support this transition at scale?
5. Customer support
1. What are the needs of your current Enterprise customers?
1. How will you scale in order to support more?
6. Revenue streams
1. Top down - ICP, key targeted accounts, ABM/pure outbound
2. PLG - Free, bottoms up, pilot + PoC process
3. Community Led - Empower people to become an extension of your brand, product feedback, customer advocacy, resellers, consultants (creating additional revenue streams)

This is a great question and a task that I was asked to take on for Vanta twice over the past two years - first helping us break into the mid-market, and later helping us break into the enterprise.

My first piece of advice is to make sure that there's cross-functional alignment in your company around the desire or need to move upmarket. It's really important that the entire company is on board with this decision.

From there, I'd have representatives from GTM and EPD take a long hard look at any "upmarket at bats" that your company has had to date, listening to Gong calls, reviewing Salesforce data, etc to see what's working and what isn't working.

You'll want to have the best assessment that you can have on whether or not your product is ready to move up market, where the gaps are (or might be), and whether or not those gaps can be resourced and built.

You'll also want to make sure that you have the best initial pulse possible on who your upmarket ICP is. i.e. How are they similar or different to your current ICP? You probably won't know this initially, but you'll figure it out.

Finally, you'll want to make sure that you're being thoughtful with how you (in sales) are going to approach generating and working these deals - probably setting aside a small team of sellers to help with the testing.

Moving upmarket is generally a tough assignment from my experience and one that really only has a shot of "working" or "feeling good" if your company allocates real cross-functional dollars and resources to it.

If you are tasked with taking the sales function up market in an existing business structure, here are some pieces of advice that you may find helpful:

1. Understand your target market: Start by researching the market that you are trying to move into. Who are your target customers? What are their needs and pain points? What are the trends and dynamics of this market? Once you have a good understanding of the market, you can develop a sales strategy that is tailored to the needs of your target customers.
2. Develop a value proposition: Based on your research, develop a clear value proposition that sets your business apart from competitors in the market. This should be a clear statement that describes what your business does, how it helps customers, and what makes it unique.
3. Focus on relationship-building: Up-market customers tend to have more complex needs and longer sales cycles than lower-tier customers. As such, it's important to focus on building strong relationships with customers and prospects. This can involve personalized outreach, attending industry events, and developing thought leadership content.
4. Invest in sales enablement: To be successful in up-market sales, your sales team will need to be equipped with the right tools and resources. This may include training on how to sell to higher-tier customers, access to customer data and analytics, and the use of sales automation tools.
5. Measure and optimize: As you start to implement your sales strategy, make sure to measure its effectiveness and adjust it as needed. Track metrics like customer acquisition cost, win rates, and deal size, and use this data to optimize your approach over time.

Remember that taking the sales function up market can be a long-term process. Be patient and persistent, and focus on building relationships and delivering value to customers.